My whole life, we've had this family friend. Not super close, but our parents our friendly and we knew each other a little bit as kids/teens. When he was moving to my city seven years ago, his parents had him reach out to me. He had a girlfriend at the time, but we caught up, I thought he was a nice guy, really positive and kind, and I said we should get together again when he moved. Neither of us followed up. We didn't see each other for two years, and then I saw him again at a mutual friend's holiday party. His girlfriend was there. I thought he was a nice guy, didn't think of him romantically because of said girlfriend. Followed up to invite him to my birthday a few weeks later... he was out of town but said we should catch up soon, and we never did. At some point, he and the girlfriend break up. I'm still single, my mom asks me if I had ever thought about dating him I say no, never thought of him like that... because I hadn't. He had a girlfriend. It just didn't occur to me. So, nothing happens. I run into him two years later again, he's really nice to me, I send him a partiful to my birthday a few weeks later... he doesn't respond. But then I start thinking over the next few months about how nice he was. And that he's a good guy. And how we come from similar backgrounds. And I realize, oh, maybe I am a little interested in him. Maybe we should go out, or I should reach out directly to catch up. But by then, he has a girlfriend. And now they are getting married this summer. Meanwhile, I'm 33 and single. I feel like on paper, we could have been a good match, we had the same background, grew up similarly, and I never got the opportunity to find out because I hadn't really thought about it too deeply until it was too late. I saw him on dating apps once or twice, but never liked him because I didn't know if I had feelings or not, thought of him more platonically and thought it would be awkward, but now I wish I had. I just feel like I could have had this really happy life with him, and I had a year or two to realize it in between his relationships, and I realized it just too late. I know guys like him are few and far between, and I feel like I blew a golden opportunity. How do I forgive myself?

I wasn't attractive growing up and didnt really get a lot of male attention. Had one boyfriend from 18-20 or so, and then didn't have much luck dating until I was 25. Met a guy. Was so happy to have a boyfriend I overlooked some red flags, and we dated off and on until I was 28. By then, had gone through the pandemic. Was exhausted and numb from the experience of my ex. But really wanted a partner. Started dating again. A year later, went on three dates with this guy who was perfectly nice. We met at a weird time. My grandpa died between dates 1 and 2, so there was a pause. He was understanding. Then date 2 happened a few weeks later, we had a nice conversation. We kissed and he tried to ask me over but I said no. Then the holidays came. Another pause. Not much communcation in between. Went on date 3. I just felt so platonic with him on that date, not wanting to kiss him and uncertain about my feelings and if I even wanted to see him again, so I said this felt more like friends and ended it.

I saw him on the apps for years. Never thought twice about it. Continued to date in maybe a stupid way. Trying to give people three dates, and ending it if I didnt feel anything by then. Meanwhile, I keep feeling "drawn" to men who ghost me, who are not emotionally available, repeating my old pattern. Have a chaotic few years between work and life. Travel a bunch for weddings and work which makes it hard to keep momentum with dating, and had a few first dates where second dates never happened because of it. Around ~31 or so, realize maybe I'm part of the problem. Revisit a man I had gone on three dates with a few months prior, ended things with because it didnt feel right, and dated him for three months. It wasn't great, I still didn't like him, and he eventually didn't like me either and we very mutually broke up. Recently, met a guy I liked. He felt calm, not emotionally unavailable. It felt steady and I was actually looking forward to going on dates with him. It felt like, maybe this is how it's actually supposed to feel, not chaotic, not stale. After our third date, he ended it with me saying he didn't feel I was the right connection for him.

I was upset. But I get that's dating. But it's made me look even further back at my patterns, and say oh shit, what about that nice man I met when I was 28? Maybe I totally messed up that situation. I saw him on the apps for years after and never reached out, never second guessed, until this week. When I realized what I really want is safety. Security. Stability. And in hindsight, maybe I didn't have a good enough reason and could have dated through the uncertainty a bit more. But I wasn't experienced enough then to know that. Of course, he is now engaged to someone he met last year. And I am 33 and still single, and feel like I totally messed up the 28-31 window, and now most stable people capable of partnership are partnered, and I'm so scared I ruined my whole life and will be alone forever and missed out on someone who could have been wonderful for me because I wasn't in the place to see it. Please help me, how do I forgive myself? It feels like I totally ruined my life with bad judgment.

I wasn't attractive growing up and didnt really get a lot of male attention. Had one boyfriend from 18-20 or so, and then didn't have much luck dating until I was 25. Met a guy. Was so happy to have a boyfriend I overlooked some red flags, and we dated off and on until I was 28. By then, had gone through the pandemic. Was exhausted and numb from the experience of my ex. But really wanted a partner. Started dating again. A year later, went on three dates with this guy who was perfectly nice. We met at a weird time. My grandpa died between dates 1 and 2, so there was a pause. He was understanding. Then date 2 happened a few weeks later, we had a nice conversation. We kissed and he tried to ask me over but I said no. Then the holidays came. Another pause. Not much communcation in between. Went on date 3. I just felt so platonic with him on that date, not wanting to kiss him and uncertain about my feelings and if I even wanted to see him again, so I said this felt more like friends and ended it.

I saw him on the apps for years. Never thought twice about it. Continued to date in maybe a stupid way. Trying to give people three dates, and ending it if I didnt feel anything by then. Meanwhile, I keep feeling "drawn" to men who ghost me, who are not emotionally available, repeating my old pattern. Have a chaotic few years between work and life. Travel a bunch for weddings and work which makes it hard to keep momentum with dating, and had a few first dates where second dates never happened because of it. Around ~31 or so, realize maybe I'm part of the problem. Revisit a man I had gone on three dates with a few months prior, ended things with because it didnt feel right, and dated him for three months. It wasn't great, I still didn't like him, and he eventually didn't like me either and we very mutually broke up. Recently, met a guy I liked. He felt calm, not emotionally unavailable. It felt steady and I was actually looking forward to going on dates with him. It felt like, maybe this is how it's actually supposed to feel, not chaotic, not stale. After our third date, he ended it with me saying he didn't feel I was the right connection for him.

I was upset. But I get that's dating. But it's made me look even further back at my patterns, and say oh shit, what about that nice man I met when I was 28? Maybe I totally messed up that situation. I saw him on the apps for years after and never reached out, never second guessed, until this week. When I realized what I really want is safety. Security. Stability. And in hindsight, maybe I didn't have a good enough reason and could have dated through the uncertainty a bit more. But I wasn't experienced enough then to know that. Of course, he is now engaged to someone he met last year. And I am 33 and still single, and feel like I totally messed up the 28-31 window, and now most stable people capable of partnership are partnered, and I'm so scared I ruined my whole life and will be alone forever and missed out on someone who could have been wonderful for me because I wasn't in the place to see it. Please help me, how do I forgive myselve

I'm about to turn 34, and I'm still single. I've been dating for about five years now. I spent 25-28 in a relationship I never should have been in that ended badly, and in hindsight, really resent losing those years where I could have met someone else. We spent the next three years keeping in touch regularly as well, which I'm sure contributed to me maybe not being as emotionally available as I thought. I've been dating pretty actively since, but nothing serious has stuck, and I'm looking at myself and my own behavior, and wondering how much of it is my fault. I'm worried I passed over guys I should have given more of a chance to let things develop, maybe because I wasn't ready or available emotionally, or was busy traveling.

For instance, some of the guys I went out with when I was about 30:

Guy 1: After our first date I thought "nice conversation but unsure about attraction"... we kinda loosely texted after, he asked if I wanted to hang again, I said yes when I'm back from an upcoming trip... and then texting faded and we never went out again (i sent the last text). He was a really bland and casual texter but nice in person.

Guy 2: I went on three dates with. I wrote: 1 date nice enough time, gonna do 2nd date. 2 - nice conversation, don’t like that he asked if I wanted to go “watch something” at the end of the date to invite me back to his, but i did kiss him and it was better than I thought, but I still felt a little weird and unsure on date 3. Date 3 I felt on fence and sort of weird. I said felt more like friends and ended it because I felt uncertain. ... but maybe I should have given it a few more dates to develop? He also was a creative, and I personally thought his creative work was sort of embarrassing/not my taste at the time, but maybe I should have separated art from artist more.

Guy 3: We went on one date. nice. Not smitten but had fun, not sure if he quite right for me, will see - could have tried second date here, but both traveling, and don’t think this was for me. We texted a bit after, but I was out of town, then he was out of town, and second date never happened. Some of his humor was a little embarrassing but nothing bad. Thought it was sort of odd he told me how much he spends in rent (a lot) on first date. He also could have followed up too?

But now looking back, all three of these guys are engaged to women and getting married. They all seemed like nice guys, who went to good schools, and two of them had good jobs. And maybe I wasn't as engaged with them as I should have been and feel like I sabotaged myself. And I am still so single, and haven't dated anyone more than like, 3 or so months. I'm wondering if maybe these are the sorts of great solid men I missed out on, and I could have been the one marrying them... and I'm not meeting these kinds of nice, solid men anymore at 34 that I was at 30. And I'm like scared I'm going to be alone because of the mistakes I made when I was younger. Do these sound like missed connections? I'm questioning if I'm even a good discerning dater anymore. It just feels like this sort of guy all settled down in the 29-31 bracket, and now I'm outside of it, and maybe the mistakes of my younger years will have consequences for the rest of my life where I may never find a solid partner because they are paired up by this age already if they are serious about partnership and would be into someone like me, or they'll want someone younger.

All to say--I have this huge partner-shaped grief now, where I'm recognizing that maybe the reason I'm single is me. And I'm deeply sad, and don't know how to hope I'll meet someone when it feels unlikely, and forgive myself for what feels like ruining the life I wanted for myself.

I recently fell for someone I met through friends. From my perspective, he's an amazing guy and has all the qualities I'd want in a partner, basically everything going for him (cute, fun, smart, kind, etc), a total catch. We ended up going on a few dates, until he decided he wasn't feeling the romantic connection he needed with me and ended things.

I am doing my best to move forward, but honestly, I'm pretty crushed. I know what it's like to be on the other side and not feel what you want or need from someone, but honestly thought things were going well with us, and that we made sense. I got my hopes up. I'm trying not to put him on a pedestal, but I'm pretty bummed that someone I saw as a good match for me, and felt hopeful about, evaluated me and said no. I know my ego is bruised, but it also is making me feel like, okay, if a guy as great as him doesn't want me, I must be lacking and not good enough somehow. Like he was out of my league and maybe I need to look for less. I can't stop feeling sad that I missed the opportunity to be with him, that I wasn't enough for him. I keep hoping for another chance, to be an even better version of myself, and feel like, maybe if I had just been a little better, played it a little cooler, he would have eventually fallen for me too?

How do I swallow this pill and get over it? I so rarely meet people that I like (I'm mid 30s) I'm having a hard time letting this go.

I'm about halfway through 33, and recently, have started to feel so old. It feels lately like a lot of the choices of my 20s have compounded. When I was younger, I still thought there was time for things to unfold differently, like in my career and romantic relationships. But as life has gone on, things didn't take the path I wanted or expected. I'm single. The career I aspired toward stalled and then didn't work out. Around me, I'm seeing friends married, have kids, moving on to the next phase. And while I hope to find that, I'm suddenly hit with the realization that it just might not happen for me. A lot of time of my adulthood has passed where things didn't crystallize how I expected, and I feel now I'm on the other side in this weird limbo. My hair seems thinner. My looks peaked at 30, and I've noted a small decline since. Life less full of possibility and more anchored to what's happened.

I know getting older is a blessing. But it's also been a lot of grief and mourning for me, for the life I wanted, and may never get, and finding myself in a place where I didn't want to be, but nonetheless am. I just don't feel as lighthearted as I used to be, and I want to be able to give off that energy again. And have hope, just in the way I did when I was younger. Anyone been through this?

A friend of mine--not a super close friend, but someone I like and play sports with and see around--invited me to his birthday this weekend at a bar. Normally, I would go without question, stop in for a drink. However, none of my other mutual friends with this guy can make it, except for his friend I recently went on three dates with, who said in the moment he wanted to see me again and suggested activities we should do together in the future, slept with me, and then pulled back and told me he didn't feel the right romantic connection for him and ended things. That happened about two weeks ago. I was a bit hurt and blindsided, because I thought things were going well, but I guess it wasn't clicking for him. Or maybe I did something on date 3 that scared him off. Who knows.

Now, I'm not sure if I should go to this party. It's going to be about 20 people. On the one hand, I don't want this guy to have that power over me and stop me from going. On the other, I could show up to this party, not really know anyone, and feel uncomfortable, while the guy who dumped me probably is a bit closer to the mutual friend and may know more people there. I know it was just three dates, but I don't know yet how seeing him will feel.

So what do I do? Do I bring a friend? Do i just skip it?

I'm 33 and have been single for 5 years. I've dated a lot in this time and gone through a lot. But nothing has led to a serious relationship. I know if I just wanted a partner, I could probably get into something, but I really want to find the right person. Someone who feels good. And I don't think I have, or they decided I wasn't a good fit for them.

I hope that eagerness for the right partnership doesn't show too much on dates, and is maybe part of why I'm still single. Because I do have a great life in a lot of other respects. I travel. I have a great family. Great friends. My career is just okay, but I am independently wealthy. I'm healthy. I know I have lots going for me. But I think it's so beautiful to have met someone in your 20s and to grow up together, share life with together, and I really want that partnership again of someone who feels like home and just makes the good things better, to have fun and live life with. It just feels like I'm missing the thing I want most.

I try to keep putting myself out there, living and dating. But 5 years now feels like a long time without anything serious. I'm working on myself in therapy as well, because whatever part of the problem is me, I want to fix.

How do I be at peace with the very real fact that actually, I might not find love again or the partnership I'm looking for? How do I not feel embarrassed that I haven't been in a relationship for 5 years or internalize that it means something is wrong with me? Or maybe something is.

I'm 33, and I recently met a great guy (also 33) who appeared to be everything I wanted. Smart, funny, fun, cute, positive, genuine, etc. Dating him, I felt something I maybe haven't felt--safe but interested and looking forward to seeing him, not feeling like I was flooded with hormones and losing my head. It felt really good and promising. And I was happy that maybe I was finally done dating for awhile.

Of course, after three dates (and sex on dates 2 and 3), and telling me on date 3 a specific date he wanted to do with me in the future, he pulls back and almost two weeks later I get a text saying he's not feeling the romantic connection he needs. I was pretty crushed, and I know it's partly my fault for being hopeful so soon.

The problem is, I can't stop looking back at everything I said and did, and blaming myself. That I am bad at dating, I presented myself poorly, and it caused him to dip. I think there may be some truth to it, because the past three first dates I went on previously all told me they "didn't feel the romantic connection" and I think maybe I am putting out an energy I shouldn't be. I can't stop replaying everything I said, how I should have said it differently, what I shouldn't have shared. I know sometimes if you share something too early when someone is still forming an opinion of you, it can turn them off.

My life the last few years has been a little turbulent. I got laid off twice, was in an accident, and now have pivoted into a new industry. I'm also pretty accomplished in certain ways. I was open that my career didn't work out as expected, and that I don't think I was even happy in my previous role, and that I think going through a layoff makes you stronger, but maybe I didn't sound settled into my new life and job, and wistful for my old career. And maybe this is all too much to share in early dating.

I've also been single for years, and wonder if I sound weary about dating. I had two serious relationships in my 20s but nothing really since. I went through a bad break up 5 years ago, have dated people since, but nothing turned serious. I want to find the right person. I think dating is hard, finding that person. But maybe it just sounded jaded, and like no one wanted a relationship with me.

I also tried to be warm and funny and engaging, we laughed and had fun too, but I'm wondering if I just seemed to broken and complicated.

I excused all his behavior (long texting delays like a day or two sometimes, forgetting things I said, not being appreciative of thoughtful gestures) as a symptom of me not being enough. And if I had only presented things with more confidence or brevity, he would have been more in.

And now, I keep spiralling on myself, convinced that it cost me a guy I really liked, who was a catch, who I maybe seemed too heavy for. And if only I had been more positive, confident, framed things better, he would have stayed. I know its no use beating myself up, but I feel like I have just sabotaged something that could have been really great by being too unfiltered, sounding worn down. And I forgot that I don't need to be dishonest in dating, but maybe I was TOO honest, and I feel horrible that I drove him away.

I know the answer here is probably therapy, but wondering if anyone has ever gone through this, and what's helped?