Building Confidence in Dating

Lisa Marie Bobby: I am so excited about today’s episode because today we’re discussing a topic that I just know is going to be so helpful for so many people who, like so many, are looking for love and for healthy, new relationships. That means today we’re talking about how to date with confidence. Every dating coach or advice columnist out there will tell you, and I think they’re largely right in some ways, that confidence is an incredibly important attractive quality when you’re out there dating. And I’m sure you’ve noticed this, in your experience that when you’re finding people that, those early stages, their level of confidence is oftentimes an attractor or a turn-off, particularly if it’s absent. We understand that we see that and other people said, we gravitate towards that sense of inner security. 

But paradoxically, dating itself is a confidence smasher for many people. I mean, you only need to have been ghosted one time by somebody that you really liked. It makes you question yourself. It’s hard to keep putting yourself out there, particularly if you’re starting in early relationships going on a few dates, it’s not working out. I mean, it’s sort of the antithesis of what any of us need in order to feel confident and secure in ourselves. To address this conundrum, and help you find some clarity and direction for how to reconnect with your strength and your self-confidence in this situation, I have invited my dear colleague, Neha, to join our conversation today. 

Neha is a therapist on the team here at Growing Self. She is also a marriage counselor, a couples counselor, relationship coach, who often works with couples who are on a quest to strengthen their relationships or improve their relationships. But she also works with a lot of people as a dating coach. People who are looking for the same thing that you are to have a healthy, happy, high-quality relationship and how to build that from the ground up. So, Neha, thank you so much for spending some time with me today. Thank you. 

Neha P.: Of course, and thank you for that introduction. I am so looking forward to having this conversation with you around a topic that feels so applicable to a huge audience. So I’m looking forward to this conversation. 

Self-Confidence and The Online Dating Experience

Lisa:  Well, it’s so relatable I mean, like every single person that I have talked with who is dating, particularly the online dating experience, it is hard. And I think it’s very common to have experiences through dating itself that damage self-esteem and self-confidence, quite frankly. I mean, I’ve known so many people that I’ve just like, given up after a while, they’re like, “I can’t handle it anymore”. They take down their profiles, “I don’t even want to try.” So it’s very real. This can look like a lot of different things for different people. But with your clients, what are some of the things that you’ve seen around that confidence in dating? What do you hear people talking about?

Neha: I feel like one of the most common things that I hear from my clients around dating, especially in this age in which online dating is so prevalent, it’s so accessible to many people. And so a lot of people are maybe venturing more towards online dating is that it’s really easy to be ghosted. I think it’s really common to be ghosted, unfortunately. I think that in itself can be such a confidence-killer because there’s this lack of closure around, “What did I do? Or what didn’t I do that contributed to us not continuing our conversation or to the conversation just ending abruptly?” 

I think that can really get into us examining ourselves, “What did we do wrong?” and ruminating on the fact that it’s about us in this moment for being ghosted, as opposed to wondering what might that other person be experiencing, if they’re even ready to engage in this type of relationship that is contributing to them ghosting you.

Lisa: It makes you question, 

Neha: It makes you question and makes you really be hard on yourself in a lot of ways, too, and really nitpick around how am I presenting during our brief conversation or even just through the stating profile?

Lisa: Yeah, did I use too many emojis? I use the wrong emoji. I mean, like it can be very nitpicky kinds of that I say the wrong thing. Yeah, wow. And at the same time, I think that should add insult to injury, people are often told that they need to be confident or to present themselves as confident in order to be successful in dating. There’s like this weird bind, this chicken or the egg kind of situation and it’s so hard. 

Neha:  It is so so tough, and I think in a lot of ways, easier said than done. When it comes to being confident, especially if we’ve experienced sort of like a string of rejection, through our dating experience. Just as you were mentioning earlier, a lot of people can sort of lose interest or desire to be dating when there has been this sort of not-so-great experience or feeling rejected in those moments. I think one thing to acknowledge is that our brain can process rejection similar to physical pain. It’s not only this, like, emotional pain that we’re experiencing, but it could be a physical pain as well for feeling overstimulated. 

We might experience headaches or tension in our shoulders, or even nausea to a certain extent. I think at times, we can also underestimate how rejection can impact us not only emotionally, mentally, but also physically at the same time. 

Lisa: That’s a really good point. Just thinking about what you’re saying, there’s like a rejection response that’s kind of like hardwired in us in some ways. Like, I don’t know, if you’ve had this experience, but I have where there’s a situation that like, in retrospect, I don’t even care that much about. It’s not a super important situation, or  I’m not deeply invested. But if I feel, rejected by this situation, or like, it’s something, I’m losing something, all of a sudden, I get activated in ways that surprised me. And I think it’s that very, like human biologically based response to a rejection, even if it’s not like a profoundly important thing. It’s just like what we do. 

In all these little, tiny micro rejections that everybody experiences with online dating, you’re saying that it can really start to take a toll even physically, that is very validating.

Neha:  I feel like giving ourselves to empathy, especially during these moments of rejection can feel so soothing towards ourselves. Not only reminding ourselves that it makes sense that you’d feel hurt during this moment, even if it’s, we say you describe like something that doesn’t feel profoundly impactful to us. But it still hurts being told no, whether relationally, professionally, in a friendship, to know I can’t hang out with you right now. No, I don’t have time to discuss this important issue that might feel important for you, that type of thing. I think giving ourselves that initial piece of empathy and validation of it makes sense that you would feel this way in this moment. Doesn’t mean that you’re wrong, it doesn’t mean that you’re quote-unquote, overreacting means that you are experiencing something, and we need to sort of honor that experience at the same time. 

It’s also a great moment for us to sort of briefly examine how might have I contributed to this piece of rejection, whether it be at the very early stages of dating, or whether it be when we are sort of like going on dates, engaging with a certain person. When we are able to examine ourselves for more of a compassionate lens, I feel like we’re giving ourselves the space to change, rather than just condemning ourselves for showing up this way. Although we want to own the ways in which we can show up just a little bit differently, I encourage my clients to not let that take up too much of the narrative that we have about ourselves, stories that we tell ourselves. 

Just because in this instance, I might have said the wrong thing, it doesn’t mean that that is who I am, it means there are moments in which I can show it this way. And now I’m aware about it. And now I can do something about it. But I think compassion is such an important tool during  the dating process, especially if we’ve experienced rejection.

Lisa: I love that positive, supportive, inner narrative, growth mindset, learning from the mistakes and with gratitude as opposed to collapsing into self-hatred, yes.

Neha: Again, easier said than done sometimes. And I think with that, it just takes practice to with thinking about how we talk to ourselves, not only when we’re dating, but also like, even professionally to within friendships, I think it’s really easy sometimes to really hone in on some of that negative self-talk, as opposed to saying, “What can I learn from this? What do I want to do about it?” So I think that can also be a great tool. It’s like sometimes challenging some of these thoughts. I always get rejected, versus “Can I think about moments in which I didn’t experience rejection, which dating did work out for me”, by reminding ourselves of these moments in which can sort of contradict that really mean voice in our head that can show up. I think it helps also process the rejection that happened and allow us to have a space to try it again.

Lisa: That’s a really good point. And I would imagine too, I think for a lot of people, because that online dating experience, in particular, is so fundamentally isolating. It’s just you with an app and the avatars and text messages going back and forth. Like it’s a very solitary experience in many ways. And I think that it can be common for people to imagine that it’s going differently for others. That other people are having an experience that is different from theirs where they may be feeling rejected, or they’re interacting with a bunch of people that don’t really feel like a good fit for them. There’s a sort of imaginary “other” that is having like a great experience and meeting wonderful people online and like finding love immediately. And I wonder if you found that to be true for your clients like they’re sort of comparing the experience that they’re having with the experience they think they should be having and that in itself is making them feel bad. Do you see that? 

Neha: Absolutely, although dating is fundamentally a way in which we’re trying to make relationships and connect with people, you’re spot on with especially online dating is an isolating process. It is us behind the screen, and connecting with another person behind the screen, or just going through these profiles, which feels just a little bit disconnected to a certain extent. We can’t really get the information that we really want, by just looking at a profile. We need to put ourselves out there and connect, which of course, is scary in its own right. And I think you’re spot on too with this comparative mindset of the guy next door who’s trying to do this is probably connecting with many people, or she is probably having such a positive experience compared to what I’m having.

And it makes me think about, I’m such a fan of asking yourself the why question: “Why am I feeling like I need to compare myself to someone else’s process?” Or “What would it be like if I were to talk to somebody who is also experiencing online dating, to help me normalize this process?” As opposed to feeling ostracized, and that I’m doing something different, or experiencing something differently than the person next door. It’s—gosh, dating is really hard right now. During COVID times, we were already feeling a level of isolation in its control, difficult to just going back to that period of like ghosting, where we can’t sometimes even get the opportunity to connect with somebody, we don’t get the chance.

Lisa: As we’re talking, I’m thinking too, about the potential for viewing the lives of other people, friends, and acquaintances through the lens of social media. Because there you see people posting pictures of like, the fun dates they’re on or cute selfies, like with together with a cute guy that they met through whatever platform. And people aren’t talking about the 150 rejections that they had on the way to creating that. There’s this tendency, societally, to amplify the positive things, which can really make people who aren’t having that picture-perfect thing to post wonder if they’re doing it wrong. If there’s like something about—do you see that as being part of the comparison process with you, I mean, you’re probably much more tuned in to what’s happening with people on social media than I am.

Comparing Yourself

Neha: I think that is such a great point, not only in dating but just like on an everyday basis. When we notice ourselves having comparative thoughts with the individuals or couples that we see on social media. I think social media is a highlight of people’s lives, as opposed to the five days that being in a relationship can feel difficult at times. We aren’t—we’re just showing the Friday night, super intentional date night that we had, and not the conflict that we had right before we left on this date. I think social media can be really deceiving and a lot of ways and it can sort of amplify those comparative thoughts that can lead to us feeling isolated, to us feeling like we’re doing something wrong. So it makes me think about when we do notice ourselves, comparing ourselves on social media to other people taking a step back and saying, “What story am I maybe not knowing about at this time?” 

It’s not that we wish relationships that we see tend to be negative or to have conflict. And that’s the reality, conflict is healthy and normal and expected within relationships and they’re not easy—dating is not easy in general. And just as you touched on, we don’t get to see the 150 rejections before it leads to that one true connection. Dating is really a numbers game in a lot of ways and so you need to be strategic but you also need to be kind to yourself at the same time.

What is Confidence?

Lisa: That’s a really great reminder, is just to not buy into the image creation that is happening and just know that there’s more to the story. That’s really good. And so we’re talking right now about ways that people can just support themselves in the difficult situation with online dating, ways of reminding themselves about the truth of the situations and not compare themselves to others. And going into this idea, more deeply now of, confidence. That can be I think, for many people a very elusive experience. I think many people, most people struggle with self-doubt, and self-esteem. 

Sometimes feeling like they’re maybe not quite as amazing as other people. I think it’s part of the human condition. Confidence is this state of being that we strive for. We’re sort of told we should be confident. And then of course, when we see confidence in others are like, “That’s how it’s done.” So can you break down in your experience? What is confidence? I mean, people who appear to be confident, what are they doing differently than people who are like, “Yeah, I’m not really all that great.” Can you just like, take us into it?

Neha: That is such a good question and such a big question, too. And so when I try to break down what confidence is or how it can present. I think part of it comes down to trust and self. Trust in our ability, trust in our power, trust in our judgment, especially too. When we notice ourselves feeling we kind of know what we’re doing or we feel like we can sort of we’re allowed to occupy space in a room. I think is kind of what it gets down to, as well.  We deserve to be in a relationship in which we are treated really well, or we deserve to have good things that happen to us. 

I think when we start reminding ourselves of our trust and self, it can feel connected to increasing our confidence in self. And I think when it comes to trusting self, I think at times, it can feel helpful to understand why maybe there are moments in which we don’t feel our most confident self, I think a lot of this can go back to some explorative conversations, either by yourself with a trusted loved one, or even professionally to around. When were these moments in which I started to maybe not trust myself in which I was maybe given messages that I should be thinking a little bit differently than what my gut is telling me. I think when we can start bringing awareness to when this first started, or what maybe patterns we can notice within ourselves, we can start to create new changes in the way that we think or experience ourselves. 

I think when we also believe that we are intrinsically worthy of respect, power, and ability, we’re starting to believe that we deserve these things rather than we need to earn these things. We deserve to trust ourselves rather than we need to earn trust in ourselves. One of the ways in which I encourage people to build confidence is — and as cliche or corny as this might sound — listing things that we like about ourselves. I think it’s much easier for us to pinpoint the things that we don’t like about ourselves, rather than honing in on the skills that we have that make us feel confident. The ways in which we can connect with ourselves or other people that bring us joy and happiness. 

Once we start to acknowledge the ways in which we are showing up in a confident way, we’re starting to see them a little bit more often. Someone who might say that I have really low self-esteem or self-confidence and I’ll challenge them or encourage them to think about a time in which they did feel confident. And then they might recall a moment that happened a day ago or three days ago or last week. I would encourage you to not only listing things but also pointing them out in the moment when it’s happening.

Lisa: That’s really good reminder, and just like retraining yourself to focus on the things you are doing right, the things you do know how to do. Because I think it’s very easy to just fall into this super focused on the negative aspects of yourself or the issues that there’s actually a lot going on. I’m just going to share something I think that our older listeners may resonate with us more because I think that this is something that does come with more age. But I think when I was younger, in my 20s I think that I thought that confident people had their act together.

They looked good, they said the right things, they seemed to just be together in a way that I didn’t always feel or they had circumstances in their lives that I didn’t have. And I thought that being confident was like creating those things. And I think one thing that has happened as I’ve gotten older is that really this idea of confidence is more around self-acceptance. Valuing and appreciating yourself for who you are, instead of try feeling like you have to be somebody different and just, “This is who I am and I say weird things and I’m kind of a mess and that is okay.”  

That is almost the definition of confidence in some ways. And I just wanted to mention that because I think especially for some of our maybe very young listeners. Well, I think that that’s a hard one insight, I think you probably don’t really get that until you get older, but I just wanted to float that so that they know it’s coming down the line is that like, self-acceptance.

Neha: That’s an important word, acceptance for self. I think there’s like a bigger movement around authenticity, which is great. And we’re also starting to notice some shifts on social media around this too, which I think is so great.

Lisa: I don’t look at social media enough to know that. Tell me what’s going on. 

Neha: I am on social media, I can tell you a ton of it.

Lisa: I can tell you, you are a young person. So that makes sense. 

Neha: We noticed Instagram posts of vulnerability of the conversations around mental health that we often don’t see. We just see the perfect days, rather than the moments that don’t feel so good. I think TikTok has really helped with some of these shifts as well, because they can’t get compared to Instagram and please let me know listeners if I’m getting this wrong. But I think TikTok has opened up a level of it doesn’t need to be perfect. I think people on TikTok  can feel silly, they can have greater conversations, they build low risks than Instagram, which are just snapshots of our life, but I think this movement towards authenticity is hopefully being introduced to Gen Z a little bit earlier than maybe Millennials or any older generations.

Lisa: That’s refreshing. So you’re saying that maybe I need a TikTok account, that will be my energetic home on social media? Do I have to learn how to dance because I don’t know about that.

Neha: I think it’s a prerequisite to be on TikTok that you have to do at least one dance. But I love that idea of self-acceptance and authenticity is sexy. It is confident being confident oneself. And I think we can underestimate the value of accepting ourselves. When we notice the person next door or the person on social media presenting to be so confident we try to recreate something that might not feel authentic to ourselves. Maybe a good question for people to consider is what does confidence for me really look like? When do I feel the most confident?

I know for myself, I feel most confident when I feel knowledgeable about something. When it feels like I can have a conversation and kind of like quote-unquote, know what I’m talking about, that makes me feel really confident. For others it might feel like if they learned a new skill, or if they’re able to perform in a certain way like that is feeling confident. Maybe relationally it’s when I feel like I can get a laugh out of somebody that makes me feel connected or confident. What does confident look like for someone relationally, professionally, in friendships, I think that’s a great way to kind of understand what are we realistically aiming for, rather than trying to recreate something else that doesn’t really fit for us?

Hang on to Your Authentic Self

Lisa: Well, that’s such good advice. And I think, especially for somebody who’s in the midst of the dating experience, there are so many things that can damage confidence. And so what I’m hearing you say is that one of the most important strategies for people to be using and remembering is that authentic clarity around who they and the parts of themselves that they really like and appreciate. And not trying to be different and that self-acceptance, and that it’s actually the path to confidence is reminding yourself of who and what you already are, and why that is a good thing. And like finding ways of holding on to that. 

Even though these experiences are intrinsically rejecting a lot of times. Do you have any thoughts or advice for strategies or ideas that you’ve found that helped people hold on to that fundamental sense of, “I am okay, even if this guy— or whatever— online didn’t know me well enough to even give me a chance to find out.” Or I think even harder for people like going on, not just one date but like six dates like it feels like it’s you’re on the on route to a new relationship and then actually it winds up not working out? Well, what would you advise somebody to do to just hang on to themselves, their authentic selves, through this?

Neha: I think first and foremost… I think it’s so important to remind ourselves that sometimes, not all the time, it’s not about you. Sometimes it’s about the person who is sobbing a relationship or ghosting you they are ready to have the relationship. They realize that this isn’t the relationship that they feel super compatible with. That expression of: you can be the sweetest peach on the peach tree but they might like apples instead. It has less to do with you and more to do with that person’s preference and somebody really loves peaches. And they’re gonna come and they’re gonna find you and they’re gonna adore you for the ways in which you show up, reminding ourselves that we are someone person and we also deserve to be picky.

We might also notice ourselves, wanting to end a relationship with somebody or not respond to someone’s conversation. On the inverse, we know what it feels like to feel rejected. So try not to reject, or ghost people, I should say, in a way that feels unkind. I think also important to give ourselves a little bit of time and space to experience that rejection or to process it just a little bit, we can learn from the ways in which we learn from quote-unquote, mistakes. We can take care of ourselves in order to feel like we are showing up in our next potential relationship in a way that feels authentic to ourselves, rather than feeling like in that phase of rejection. If we aren’t, connected back to ourselves, before we engage in, we could ultimately end up hurting someone else in that process. So we definitely want to be mindful of that.

Lisa: Say more about that — if we’re not feeling fully like ourselves, we might wind up hurting somebody else. And what did you mean by that?

Neha: Yeah, so I think about experiencing rejection, and I might notice myself having lower confidence, reexamining myself, maybe feeling angry, or frustrated to a certain extent too. And then potentially wanting to hurt someone the way in which I felt hurt. Regardless of what the person did, or anything like that. Or we can show up disconnected in a conversation. We can show up emotionally not curious about the person — guarded is the perfect word — we can feel guarded in our presentation. And then the next person is going to think, “Well, what am I doing wrong in order to cause this person to respond this way?” So it’s kind of like this domino effect that we can maybe notice or be contributing to this dynamic that is experienced within the dating world. 

In order for us to feel like we can reengage in a potential conversation with somebody else, I think it’s so important to give ourselves some time, and yet time doesn’t heal all, it’s what we are choosing to do with that time.

How are we reflecting back on our experience in this? What are we doing in order to take care of ourselves? Sometimes compounding rejection can lead to unhealthy coping mechanisms, anxiety, and negative self-talk these types of things. I would encourage individuals to potentially if there are dosing themselves in a lower space for an extended period of time, and it feels intense — seek a professional to a therapist or coach, somebody who can help them sort of untangle the meaning that they’re making around rejection in order to continue forward.

Lisa: Yeah, well, that’s a good point. I think we’ve all been there, that negative loop starts in your head. The problem is that it feels true and it can be — no matter what you’re looking for, you will be able to find evidence of that. I think it can be hard to get out of that kind of mental rut if you’ve been really like berating yourself or being harsh with yourself. It can get very easy to get tricked into believing the things you think and the things that you feel. They’re not all helpful. 

When it comes to the dating process itself — I’ve heard you talk about some of the things that you try to teach your clients around this. We have our little dating coaching program, and like one of those first foundational steps is really getting clear about who you are, what you want. How do you think that that helps people hold on to their confidence and empowerment just right from the get-go?

Neha: I think when we have clarity around what our intentions for dating are, we can experience dating in a little bit of a more structured or intentional way. And I know I’m using that word left and right, but I really mean it. If we are clear around the type of relationship that we want, or why we’re on the app — are we seeking a long-term relationship? Are we wanting a physical relationship with someone? Not only are we being clear with our intentions, but maybe we can also communicate those intentions to someone else. If people were to engage in online dating, and we’re noticing transparency, we’re noticing honesty, that in itself is confidence building.

I don’t need to pretend what my intentions are, I know what my intentions are. I am on this app because I want a long-term relationship, not because I just want to chat with someone endlessly or just go on dates type of thing. I think when we’re also exploring what has really helped or what has worked for us in the past, that can help with confidence too, If we reflect back on what relationships have really worked for me in the past, or what traits within certain relationships have worked for me. And maybe if we don’t have as much dating experience or relational experience, we can be thinking about, “What type of relationship do I deserve to be in?” 

I intentionally use the word deserve with my clients versus what type of relationship do we want. Because when we think about deserve, I think we’re able to notice that we have worth. We have self-worth not only as an individual but as a person as part within a relationship. We’re able to examine just a little bit differently of “I deserve to be treated well.” I deserve to have someone who openly communicates. I deserve someone who understands my triggers, rather than I want a relationship that has good communication — which are important — but we’re able to just understand a little bit more when we use that word deserve from my experience.

Repairing the Damage Done on Self-Worth and Self-Confidence

Lisa: Well, that’s a nice reframe that what you desire compared to what you deserve. Although I’m thinking that — well, and that’s probably a topic for another day, Neha. I was thinking about, that it’s not uncommon for some of the people that we work with to have had relationships that were really toxic in some ways and where regrettable things happened. And over the course of those relationships, sometimes made to feel like they didn’t deserve more. And I know that can take a lot of different forms and again, topic for a different podcast. 

But I guess I’m curious to know, I would imagine just because of understanding that and knowing people that in your work as a dating coach, and I use that term sort of loosely, and you say euphemistically because you’re really a therapist, right? Like, I’m wondering how often you spent a lot of time with people just working on those like foundational self-worth repairing some of the damage that has been done in previous relationships. Maybe even a long time before we even think about posting a profile on a dating site? I mean, how common is that? Would you say it in your work?

Neha: I could maybe honestly say almost every single person that I work with, in dating coaching has experienced hurt in a relationship before or through a dating experience. So part of what it’s like clarity, or working on ourselves is increasing self-awareness within our previous relationships. So what parts of our previous relationships is still very difficult? What types of difficult moments do we not want to experience again in a relationship? By talking this out by processing, we’re not only wanting to untangle some of these false narratives that we can have about ourselves or hurtful narratives, I should say. But we’re also being mindful of what types of like red flags we need to be mindful of avoiding in the future. 

I think part of a lot of people’s experience, especially at the beginning of a relationship, or within dating is having rose-colored glasses on to a certain extent where we’re just seeing the really great things in people which is important to acknowledge. And we also want to be mindful of not letting things slide that feel like a deal-breaker to us, just because we’re connecting with this person. It might not be that you need to completely dissolve the relationship, but it would be a great cue for you to say something.

“I feel hurt. When you talk to me like this. I’m wondering if you can say it a little bit differently.” Or  “I feel disconnected to you when we go days without talking.” What do you think is a communication strategy or schedule that we can both feel comfortable with? A lot of people that I work with have described themselves as not wanting to present as too needy within relationships. Which I think is such an important word to break down a little bit more. 

I think there’s a difference between being “needy” and having needs in a relationship or as an individual, which we all do. Asking your partner for  a scheduled date night is not you being needy, it’s you having a need within a relationship. I think that can also help build up confidence around communicating our needs feeling like we deserve to be in a relationship in which I feel safe enough to express my desires to this person or that I have these thoughts, feelings. What I’ve noticed with individuals who might notice themselves not verbalizing their needs or desires as much, is resentment can be built up not only for the person but themselves for where the relationship ended up. 

That is something that I also think as we reflect back on previous relationships, were there moments in which you felt like you couldn’t communicate what your needs were because you didn’t know how partner was going to interpret that. And sort of reworking and building up some of those like healthy communication skills, healthy relationship traits as well.

Lisa: There’s so much good work to do. And I’m just thinking about the wisdom of what you’re sharing. I mean, really, helping people be very clear and assertive, and feeling able to talk about how they feel and what they need just in that spirit of authenticity and confidence. And this is actually who I am and this is really what I want in a relationship. And just the wisdom of doing that early and often, particularly in a new relationship. Because the alternative is not talking about that, pretending to be somebody that you’re not, feel a different way than you actually do. And having this relationship really be built on a foundation of inauthenticity and hiding. 

I’m imagining that that probably turns into a really nice reframe with your clients of somebody who has actually been talking about who they are and how they feel. And the other person is like, “I think I don’t want to date you anymore.” Instead of that being perceived as a rejection, having it feel like a, “Thank God, that that didn’t get any further than it could have because that would not have been in a good relationship for me.” I mean, like to really have that be a very positive reframe.

Neha: That really comes back to compatibility rather than you doing something wrong. It is not wrong for you to be authentic, or to communicate, that just might mean that we have different alignment when it comes to how we communicate, or what our long term expectations are in a relationship. We’re able to set to communicate those things that we need earlier into the relationship, just as you described. We’re able to set the scene for what we hope this relationship can or might not turn it into.

Lisa: I’m thinking right now of some business advice actually, I once received, which is irrelevant, it’s this idea that you should fail fast. If something isn’t going to work out, you find that out as quickly as you possibly can and just be done with it — fail fast. I’m hearing that that same principle applies to dating really. Your job is to figure out swiftly who is incompatible with you and be done and not like so that it sort of liberates you to continue your search as opposed to doing that thing that people do, which is, well, “If I was different, maybe that would have worked out.”

Neha: So applicable, not only in the business world relationally., professionally, with friendships, too. I love the idea of, “It’s okay, that it’s not going to work out with this person.” It doesn’t mean that something’s wrong with you, something’s wrong with them, it just means that we try again. Dating is really a numbers game in a lot of ways. We want to filter, and we want to filter fast. 

When it comes to conveying the things that we want, a lot of people will wonder, when do we start having these conversations? When do I start saying, “Yeah, I want to have kids.” This feels important relationship. That is an important thing to consider, too, when it comes to being authentic, but also being mindful of when you’re introducing these bigger topics into a relationship.

Difficult Topics in Dating

Lisa: Well, let’s talk about that. And I know that this is kind of going into the nuts and bolts of good dating strategies. While we’re here together, how do you help your clients kind of figure out that balance? Because on the one hand, we do want to be authentic, and in a confident way, showing up as ourselves. And at the same time, not leading with a weird stuff. So how do you help people sort through that and figure out what the balance is?

Neha: Well, one reminder that I like to share with my couples that I got from you, Lisa, is the goal of a first date is to see if you want to have a second date or not. So when they think—

Lisa: Oh, great, I remember that. But it sounds really good.

Neha: It’s so helpful for people to think about, when we go on a first date, it’s not that we need to start planning our life with this person. It’s that we need to examine, do I enjoy this person’s company? Do I feel like there could be a potential for us to connect again, or to connect one month down the road — something like that — as opposed to feeling like the first date is where I need to know if this is my life partner or not. I think that helps relieve some pressure. That is a lot of pressure to have on yourself to try to figure that out within one date. I think when it comes to introducing some of these conversations, I would encourage very practically to not have some of these conversations on the first date, maybe even on the second date. But maybe as we start to feel comfortable with this person.

And we want to understand like, “Does this person have similar values as me? Does this person have similar lifelong goals? Does this person want to be working for the rest of their lives? Or does this person want to quit their jobs tomorrow and travel the world with me?” Like we do want to understand, do our lifestyles sort of match up? And I think that is a great conversation to have a little bit earlier into the dating process at a very high level.

“What do you see yourself doing 5-10-15 years?” So if you see yourself traveling the world, how do you imagine yourself potentially starting a family if that is part of the conversation. I think there’s a way to have these conversations in a way that feel like it flows into the conversation rather than it feeling like a job interview and saying, you want to have this does this feel true for you? That type of thing.

Lisa: That’s such great advice and you’re really talking about discernment. And, yes, do you like this person enough? Do you enjoy their company in a general sense enough to want to hang out with them again, and then it’s, do I like this person enough to be talking about myself and my values and my kind of hopes and dreams for the future, and that it does take a long time to get to know people. And you’re sort of advising this stance that I think is extremely appropriate, which is like, “I’m still checking you out. We’re getting to know each other,” and this occurs over multiple interactions. But I think so often the case, and particularly when I talk with people who are really struggling with dating, they’re not doing that. They are getting swept away by feelings. 

The first date lasts for 72 hours. They are — and not to sound moralistic because it’s not about that — but like having sex with people that they’ve just met. They’re not thinking through it. They’re basing their responses on highly emotional factors that generally have no bearing on whether or not it’s going to be a good relationship. I think that can really obscure a lot of things. Jumping into the deep end can really prevent people from doing what you’re suggesting, which is, are our values compatible? What is this person’s character? What do I want and deserve and is this person fundamentally capable of doing this with me? Or are they just hot and superficially charming? Because there’s a time and a place for that too. Is that what you’re describing?,

Neha: Absolutely, going back to that piece of clarity of dating with intention. If I am dating in order to have a long-term relationship, then what subliminal messages am I conveying to this person and very transparent conversations am I also having with this person. Just as you said, there’s a time and a place to meet with someone just for a physical relationship, and that is perfectly fine. But if you’re wanting to have a long-term relationship, then maybe we want to go into this first date, with some intention, or some boundaries around when we plan on ending the date, when we want to plan on reconnecting with this person. There’s a difference between playing the game and feeling like you aren’t putting effort into connecting with this person. 

When there are rules around waiting three days before you text somebody. I think, to a certain extent, if you’re dating with intention, there isn’t really a need to play games, especially if the other person that we’re wanting to seek out is also ready for a long-term relationship. We’re wanting to feel like we can authentically reach out to this person when we do want to connect with them, rather than feeling like we need to wait X amount of hours or days.

Red Flags in Overconfidence

Lisa: Yeah, that’s a really good reminder. And then one last, and I know we’re coming up on our time, but one last question on the subject of confidence in dating. I feel we would be doing a disservice to our listeners if we didn’t address: is that, you and I both know from our training and our background is as therapists, that sometimes people who seem the most confident, are very charming, they’re very witty, they look good, they smell good. They have the trappings of success. There’s actually a correlation between those qualities and things like antisocial personality disorder, and narcissistic personality disorder. Sometimes the people who seem the most confident and attractive early on, are the ones that you should actually work really hard to stay away from. 

Are there any recommendations or pieces of advice that you can give our listeners certainly for them to be more authentically and confident in a healthy way? But being able to sort of discerning, as you said earlier, a potential red flag or warning sign around what antisocial personality disorder can actually look liken on the first date — highly attractive. How do you help people parse through that?

Neha: I encourage people to consider if the person that they’re talking to is as interested in learning about you as they are interested in talking about themselves. Sometimes we can experience a person just wanting to talk about themselves or asking you questions in order to just give you their answer. I think that can feel like a red flag when it feels like there is an imbalance in the desire to have this kind of conversation, the desire to get to know one another. I think that is one to definitely look for when it comes to red flags. I think also self-awareness is something that feels so important to have within a relationship. 

People will ask me all the time, like, “How do I know if a person is the one?” And I’ll always say,  “Does this person have a desire to grow and change with you? And does it feel like long-term values needs, goals are aligned?”  Thinking about that first one, it’s not about them completely over apologizing, or being super hyper-vigilant to the ways in which they show up. But saying, “You know what, just a second ago, I said something, and I wish I could take it back, because I actually meant this”, or “This is what I’m actually trying to convey,” or “I apologize if that hurt your feelings. Here’s what I meant to say.”

I think if a person can communicate that level of self-awareness, or maybe if even if that level of authenticity shows up for you, and you say something like, “You know what? Help me understand what you mean by this.” And they’re able to examine why you might be answering that question. I think that’s a great indicator of having that level of self-awareness. And so the opposite of that lack of self-awareness, lack of accountability is also a red flag.

Lisa: That is great advice that if the other side of the table is similarly confident in an authentic way that is based on self-awareness and personal responsibility, and taking ownership and being vulnerable, that’s a good sign that it is genuine, healthy confidence, versus one that feels fragile or potentially harmful. Because people can be very confidently love-bombed and be swept away, and not until a long time later be like, “Wow, that was not what I was looking for.”

Okay, I just wanted to talk about that a little bit. Because, again, the topic of confidence in dating. There are other elements of this for people to be aware of, but thank you for spending this time with me today, Neha, this was such a wonderful conversation. I am so appreciative just of all of the really good insights and also like the actionable ideas you shared with our listeners today. Thank you.

Neha: Absolutely. It was such a pleasure. And as a final reminder that dating is hard and it takes time and it takes confidence and you can do it.

Lisa: What a wonderful — I think people need to be reminded of that, to keep going. Oh, good. Thank you again for doing this with me and we’ll have to visit another time. 
Neha: I would love that. Thank you so much, Lisa.