Sad About Being Single?

The Love, Happiness & Success Podcast with Dr. Lisa Marie Bobby

Are you Single and Sad?

Modern dating is complex and challenging. As a dating coach, I receive questions about dating every day, and I’m always happy to offer my honest dating coach advice!

I’ve had so many listener questions about dating coming in lately that I just had to address them on a podcast! In particular, we’re diving deep and talking through some of the more complicated aspects of “dating life” that many people struggle with. 

The rest of this post will give you an idea of some of the questions asked. For the complete answers, check out the full podcast at the end of the article.

Single And Sad

Are You Sad About Being Single?

Many people are bravely putting themselves out there but feeling discouraged that they’ll never find “the one.” 

On top of the normal frustrations of dating, there’s a hidden emotional complexity here: They feel sad about being single. Like, really sad. Days like Valentines Day feel depressing and lonely. They watch coupled people longingly and may even find it difficult to be around couple-friends.

How To Not Feel Sad About Being Single

When you often feel down about your singleness, it’s hard to put on a brave face and be the sparkly, fun-loving person you feel like you need to be to attract someone new. They don’t know how to be single and happy, which paradoxically makes finding love more difficult.

A listener wrote in sharing that she was feeling so triggered by her couple-friends and depressed about being single that she felt herself withdrawing from activities she used to enjoy. She asked, “How do you cope with intense feelings of sadness about being single?”

I addressed this question in-depth on the latest episode of the Love, Happiness and Success Podcast. (Hint: The punchline is NOT about how to be happy alone — just the opposite!)

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Dating After Divorce

Here’s another great question I received about dating: 

When Are You Ready To Start Dating After A Divorce? 

Another listener wrote in asking how to know if it was okay to be dating another recently divorced person or if he was rushing into things too soon? 

On the podcast, I talked him through some of the pros and cons to consider to help him decide if dating was a positive thing for him…or potentially interfering with his process of growing and healing after divorce.

I also shared some insights into the positive aspects of starting a new relationship after a divorce. As well as what kinds of personal growth work may potentially be blocked by jumping into a relationship too soon after a divorce. I also address what kinds of personal blind spots that—if unaddressed—may lead to a less successful new relationship going forward.

Dating As a Single Parent

Yet another listener asked:

When Should You Tell The Kids About A New Relationship?  

Modern dating can be complicated enough, but if you’re dating as a single parent it can add a whole new layer of complexity to your feelings about someone new.

A podcast listener wrote in, saying that he’d been dating another single parent for some time, but he’d become increasingly concerned and frustrated with her because she refused to tell her children that she was dating him.

On the podcast, I talked about a few of the things that she might have going on behind the scenes (and that all parents who are dating should be aware of, frankly) to point out some possible reasons she may not be comfortable telling the kids about this new relationship. 

I also touched upon some of the ways that he might communicate with her about this subject without starting a fight, and that will help him determine if this is a relationship he’d like to pursue. (Or whether he’s with a person who isn’t emotionally available for a relationship right now.)

Daring To Trust Again

I’ve also heard from a number of listeners lately struggling with this question:

How Do I Trust Someone New After Being Cheated On?

If you’ve been hurt or betrayed in a past relationship, it can be very hard to even want to date again, much less trust again.

On the podcast, I describe what the process of healing after betrayal looks like, in order to give you an idea of some of the personal growth work you might need to do before dating again. It’s important to have a solid emotional foundation for yourself, so that when you do start seeing someone special you are dating from a place of strength and self-awareness.

I also talked about how to regain a feeling of safety after being betrayed—particularly after you’ve been cheated on in the past. One side of the coin has to do with cultivating confidence in your own judgment, and the other involves learning to recognize the red-flag attributes of a person who is likely to cheat on or betray you in the future.

All that, and even MORE of your dating questions on this edition of the Love, Happiness and Success Podcast. Thanks for listening!


Dr. Lisa Marie Bobby

PS: Do YOU have questions for me about dating, or anything else related to your journey towards Love, Happiness and Success? I’d love to hear them, and just might answer them on an upcoming episode of the podcast, or in a new blog article or IGTV video. 

You can ask YOUR questions either in the comments below (I read every single one!) or by submitting your question through this secure online form. All the best, LMB

PSS: At least for the next few weeks, I’m going to be recording new episodes of the podcast LIVE on Instagram so that I can answer listener questions in real-time. I hope you join me! @drlisamariebobby, every Monday at 12pm Mountain. Hope to see you there!

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Sad About Being Single?

The Love, Happiness & Success Podcast with Dr. Lisa Marie Bobby

Free, Expert Advice — For You.

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  1. Being a single man is certainly no fun at all these days either. A very excellent reason to hate the holidays when they come around.

  2. Being a single man is certainly no fun at all these days either. A very excellent reason to hate the holidays when they come around.

  3. Holidays can be especially hard Jim, you’re absolutely right. I hope that you make a good self-care plan this year to help you get through them. Also please know that many others are feeling the same way, and that’s why dating during the holidays can actually be very fruitful believe it or not! More on the subject if you’re interested….

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