Feeling self conscious about dating history

December 31, 2021 11:18 PM

In my life I've generally been pretty unsuccessful with dating, such that I find myself having reached my late/mid 30s and now am in the bracket where I just feel like my dating experience is way different from a lot of the people who might generally be interested in me. How do I approach conversations about dating or past relationships with these people I might meet as I soldier on in this dating world?

I guess this question still could have been a thing anytime in the past 10 years really depending on who I ended up dating but as I sort of wander into middle age and start dating men in their 40s more often (I'm a cisgender/straight woman), it feels like the imbalance of my relationship experience versus theirs is growing. The longest relationship I've had was 5 months. Aside from that, mostly I've dated various people for maybe 2-3 months at a time, in addition to the many people in the 1-3 dates longevity range.

I don't really have a great explanation for why nothing has worked out. I could offer up that I struggled with my weight when I was in high school and had low confidence so didn't really date then. Then once I did start dating I think the low confidence and inexperience thing plus a tendency to get hung up on people who weren't really into me meant I picked either unavailable people or jerks (or unavailable jerks) for a kind of long period. Maybe I was a slow relationship learner? Then I had a job that had me traveling a lot. And I'm pretty introverted so don't get out and meet people as much as some others might. And I don't know, I just don't feel like I meet people that I'm actually into (and who are into me) that often, despite pretty much continuously being on dating websites. The person who I had the longer and more official relationship with was in the end a bad fit for me and kind of a bit unstable of a personality who I would not want to do something like raise kids with or be tied to long term in the end.

Anyway, it feels like how much I end up talking about past relationships with people I'm newly dating really varies. With some people, the subject barely comes up. But with others it ends up being a bit more of a thing, or just comes up in conversation and they seem curious about my history. When people start asking questions about when my last relationship was or my views on relationship questions, I just feel a mix of embarrassment and I guess uncertainty about how to respond. It feels like kind of a sore spot that I don't really want to get into when I've just met someone but even giving the basic facts that I haven't really had anything long-term before might cause someone to be curious or raise an eyebrow.

And then there is the fact that even if I don't ever at any point end up having an in-depth conversation with someone about my dating history, I feel like someone who has had some long term relationships or even been married before must just have much more in-depth understanding of how they operate in relationships and what they like and don't like and what they are looking for. For me, I certainly have ideas about the kind of person I want to date and about things that seemed to be a deal-breaker for me in my previous shorter relationships. And of course I interact with humans in my life and have non-romantic relationships where I've hopefully matured over the years in terms of my social/emotional intelligence and ability to communicate. But it's not quite the same as building a long-term romantic relationship, and I feel like there are some things you don't know about your views on certain situations until you've experienced them yourself. I feel like I WANT a long-term relationship and I've always wanted that, but maybe once I'm in one I won't know exactly how I want it to go or function or something. In the one more official relationship I did have, I guess it didn't seem like that big a thing, but once things were official, I feel like it was taking me a while to sort of make a mental switch to being part of a couple. I'm just used to being pretty independent. Despite really wanting a relationship, I feel like slower could be better for me, as long as the relationship was actually going somewhere (I've had a couple of dating things the past year or two that just went at a glacial pace due partly to COVID and then sputtered and didn't turn into anything) - so I could kind of ease into the being in a couple thing.

I guess this question was tipped off by a recent dating experience where the relationship question did come up relatively early on. I feel like it's kind of kicked my anxiety into gear and am trying to sort out in my head how to approach any future conversations, either where I'm prodded further about my relationship history, or where the other person wants to have some kind of discussion about my thoughts on relationships in general, a discussion for which I feel ill-equipped along some lines. Thoughts? Particularly interested in anyone who has dated someone with significantly less relationship experience than them, or has been the person with less experience.

posted by anonymous to Human Relations (15 answers total)

Sara Eckel has a good essay about this--NYT link, though. But here's what you need to read:

"Mark and I dated for a month before I revealed my shoddy relationship résumé. When I did, he shrugged. “Lucky for me,” he said, “all those other guys were idiots.”
And that was it. To Mark, I was not a problem to solve, a puzzle that needed working out. I was the girl he was falling in love with, just as I was falling in love with him.
Six years later, this past June, he and I celebrated our first wedding anniversary. My close friends — the ones with whom I had shared many impromptu therapy sessions — had come to the wedding in a small Brooklyn park. And so had their husbands.
Did we find love because we grew up, got real and worked through our issues? No. We just found the right guys. We found men who love us even though we’re still cranky and neurotic, haven’t got our careers together, and sometimes talk too loudly, drink too much and swear at the television news. We have gray hairs and unfashionable clothes and bad attitudes. They love us, anyway.
What’s wrong with me? Plenty. But that was never the point."

As for me: I had a few boyfriends and then as it turns out, literally nobody has wanted me for 18 years and the one guy I asked out ah, didn't want it to be a date. So if I ever have that conversation, nobody can possibly top me for how awful that's going to be. You won't be as bad as me, if that helps any.

Unfortunately, "why I haven't had more or longer relationships" ALSO depends entirely on the other person involved and what they want to do. It's not 100% under your control. All you can really say is, "I tried, they didn't want to." There's well...less good guys out there to pick from than good women to boot, as well. I really do think you get lucky or you don't (obviously I have not) on finding one.
posted by jenfullmoon at 12:50 AM on January 1, 2022 [18 favorites]

Personally when someone starts asking about my relationship history early, I bail. In my experience people who do this are just fishing for personal info, trying to expedite the intimacy building process and interviewing you as a dating prospect, rather than actually being interested in getting to know you as a person. With the people I’ve had the best connections with and who genuinely liked me and weren’t interested in filling a girlfriend-shaped hole, it actually never really came up in the dating phase. Incidentally, these also ended up being the most interesting and emotionally rich guys who had interests, were well read, and could chat about a variety of things.
Obviously you may not want to eliminate people based on this question being asked, but I do, and I’ve never had any regrets about it.
I’ve also seen people with a “normal” amount of relationship experience act like complete idiots, so while it may make them more comfortable in relationships, I’m not sure experience inherently makes someone some kind of relationship savant.
posted by cultureclash82 at 3:55 AM on January 1, 2022 [13 favorites]

My relationship history was pretty similar until I met my husband when I was 35. I mean except I didn’t even have any five month relationships. We never talked about it much and I don’t think he cared? We just felt really lucky to have found each other. He died a little over a year ago (we were together for seven years) and I do kind of wish we had talked about our relationship histories more once we felt secure with each other, but it turned out we didn’t have time to get to everything.

As for my understanding of why I was “like that” before I met him, I struggled a lot with social anxiety when I was younger and I loathe dating, which I think mostly explains where I was coming from. Also I think at some point I just stopped being interested in a conventional couple relationship in and of itself, to the point where someone had to be really awesome for me to be interested in getting into one (my husband was sufficiently awesome).
posted by mskyle at 6:36 AM on January 1, 2022 [9 favorites]

I don’t think you have to talk about this until and unless you want to. No one is entitled to these “basic facts” (that are actually very personal and intimate details) about you. A Mona Lisa smile, “Oh, I don’t like to talk about my exes” and a ready change of subject should get you through fine. And you do know what you’re looking for in relationships and can answer those kinds of questions. “I’m looking for something long term. I’d like to take it slow and steady.” You can answer questions about your relationship preferences, dreams, desires, and deal breakers with confidence. It’s true that you might be *wrong* about the answers to some of these questions you answer confidently based on what you think now — but that’s true for anybody. Each relationship is a custom job, it turns out, so what works in one might not in another. So all any of us can do is give our best guess at the time.
posted by shadygrove at 6:50 AM on January 1, 2022 [15 favorites]

I think often when someone asks about your dating history, what they are asking is if you have a recent ex you may be still invested in or someone you are pining over. They want to know if you’re emotionally available or not. Or they’re newly divorced and want to know if you are because recently divorced people want to talk about divorce. So you can answer with your recent history, something like, “It’s been especially hard to connect during Covid, I met a couple people but nothing that worked beyond a few weeks.” Hopefully they can relate to that and you can share some anecdotes about dating or socializing during Covid.
I think your dating history is very normal! In my circles, people either met a partner during early twenties or didn’t (and then half those people split up with that partner in their thirties). Often someone who is divorced only has much experience with one partner, so it’s not like they are skilled at relationships or dating, they are only “skilled” with that one or maybe two people.
posted by areaperson at 7:59 AM on January 1, 2022 [19 favorites]

This is pretty normal actually! Certainly not damaged or weird. I would just say, "I haven't felt the right fit to get really serious with anyone before". I don't think this would feel like a huge red flag to most guys. As long as it's clear you're not in love with an ex, they likely won't care and may even see it as a positive that they can be the "first" serious relationship you experience.

>I feel like I WANT a long-term relationship and I've always wanted that, but maybe once I'm in one I won't know exactly how I want it to go or function or something.

Long term relationships are not that different than other relationships. I think they're mostly only different in that people get less conscientious and somewhat more annoying as you know them longer (lol) so you need to learn to communicate, advocate, overlook and forgive a lot of little annoyances like household chore splitting. But those annoyances can be balanced by deeper love of each other so it can work out.

When it goes well, a long term relationship is kind of like the blend of tolerance / annoyance / love that you'd feel about a close friend, roommate, or co-worker. In some ways it's even like how you feel about a sibling or pet - they're great, they're infuriating, they're more-or-less here to stay, sigh, thank goodness, eyeroll forever, if I have to clean up your pee again I'll murder you, come snuggle me ya big lug, etc. But a partner can be better than a pet because they understand language, and better than a boss because you're truly peers, and better than a friend because sex is fun and can help glue the relationship back together faster than many other forms of reconciliation... so if it's a good match, it will be even more durable than most of your other social relationships in the past.

But also, it does bear saying, careful what you wish for, because as a woman, you may not actually be better off partnered with a man. Men are socialized to take huge amounts of uncompensated labour from women - ponder the "emotional labor" thread on this site for clarification - so women need to have extra-strong boundaries, communication, self-awareness for division of labour, and one foot out the door faster than men need (and even still, it's like 99% likely that he won't listen and he won't change, no matter how good you are at identifying and communicating that it's a problem). Marriage is a great situation for a man... and it is a heavy weight on a woman's back. For a woman, to be totally honest, I'd say that a male partner is not as good as an excellent female roommate or a female best friend. Because as a woman married to a man, you will do more than your share of the work, all the work, for-effing-ever, and that will never ever ever change. So traditionally the tradeoff should be that he contributes more money- but that often isn't true any more now that women in some fields are achieving pay equity in the workforce. And you may find that when you clean up after someone AND you manage the household AND you have a job at which you out-earn them? You may not feel you're getting a great deal at all. A lot of women I know are feeling this, hard, as their marriages hit the 5-10 year mark, and they are not wrong.

All this to say that it's likely that your life experience has already taught you quite a bit about how to get along with someone long term. Whether or not you actually WANT to is the part that's hard to gauge until you try.
posted by nouvelle-personne at 10:33 AM on January 1, 2022 [16 favorites]

I could have been you - I remember pretty much the exact feelings you describe. I don’t remember actually discussing relationship history on dates (and therefore what I said), but presumably it happened. The suggestions above to just say something like, “it just hasn’t worked out yet” seem reasonable to me. No need to apologize for anything or explain in detail in early conversations.

I met and started dating my now-husband when I was around 42; he is a couple of years older. Neither of us had had much long-term relationship experience before we got together. Like you, I also felt like I was missing some “relationship skills” that could only come with experience. Turns out he was too, and we have developed them together. And yes, our relationship developed pretty slowly.

(Re emotional labor, since it’s come up - in my relationship my husband does more of the emotional labor.)
posted by argyle sock at 12:10 PM on January 1, 2022 [2 favorites]

When I meet people who don't have a lot of relationship experience, I assume they are independent and not willing to settle, and I consider those great attributes.

I also think that older people are on average less likely to want to completely enmesh their lives with a partner; we recognize that we have our own lives we want someone else to fit into, rather than throw away what we have. And if that's what you want, you should focus on people who are on the same page.

RE asking about past relationships, I do, because I am curious about people's lives and our romantic partners are often big parts of them. I also ask where they've lived before, if they went to college, whether they have siblings, etc. If any of those kinds of questions don't lead to interesting conversation, we move on. I can see why it would be easy to see asking as judging, but odds are good that they are NOT dwelling on the fact that you don't have much you want to talk about in some of those categories.
posted by metasarah at 2:40 PM on January 1, 2022 [2 favorites]

I could have written something very similar a little over five years ago, before I started dating my current partner. I also don't think you're that unusual, at least among my peer group.

I agree with those saying that questions about dating history are not a red flag per se, and can be easily deflected. One does generally learn things about themselves through dating people, especially in terms of what they want (or don't want) in relationships, and so it's understandable that some people like asking about one's past. Another way to deflect could be "Oh, I'd rather not get into specifics at this point, but I'm happy to talk more about what I'm looking for or what doesn't work for me, etc." If someone doesn't respect that re-direct, that's a red flag.
posted by coffeecat at 4:24 PM on January 1, 2022

I just dropped in to say, in case it helps: I'm not sure your lack of a long relationship puts you at as much of a disadvantage as you think. I'm in the opposite boat, having had basically just one decade-plus relationship, which I ended recently. It's true that I learned a lot about myself and what I do and don't want in a relationship...but it took me years and it was really messy for me and I'm not sure how much it helps with future dating, y'know? Everyone is so different. If I do wind up with someone else, I am going to have to negotiate everything anew, and probably be worse at it than you since I am so out of practice! Wishing you much success.
posted by ferret branca at 4:34 PM on January 1, 2022 [2 favorites]

I am also not sure that being in a relationship for a long time is necessarily, like, a virtue. I mean, if you want it to happen, I hope it works out for you, but I honestly probably should have ended things sooner. I wish society didn't treat A Long Relationship as something that is inherently the most worthy.
posted by ferret branca at 4:36 PM on January 1, 2022 [3 favorites]

you not only can but I think should be extremely vague about your dating past until you're in a relationship that's secure and established enough for you to feel comfortable giving real details with emotional significance attached. I don't think I ever ask guys this unless they ask me first, and I don't think I've ever been asked for like a full history, job-interview-style (nor would I provide one). usually it's just a tentative question about the most recent relationship I/they had. and the one way it is like a job interview is you can leave out experience that doesn't make you a more attractive candidate; if you don't want to talk about it, it's not their business to know.

the only bad answer, and I think this goes for men and women equally even though I only date men, is one that has a lot of intense emotion attached to it. any kind of emotion - "oh how I hate my horrible ex-wife" is at least as bad as "oh god I miss my wonderful ex-wife", you know? and "Had a few good relationships but they didn't really work out in the long term" is fine where as "I've dated a lot of people but I guess there's SOMETHING about me that's not MARRIAGE material" might make you edge away.

a few months counts as a long-term relationship for the purposes of talking to guys you barely know, and I personally think that exaggerating three into six months, or six months into a couple of years, is a completely acceptable lie. men who are psychologically ok and good to date aren't asking you this to be competitive about who's seen more people or who's been married more, they're asking a. to make conversation and b. to see if a standard question provokes some unusual or extreme reaction. I think it is more important to be neutral, off-hand, and unashamed about your answer, no matter what you say, than to give any particular answer.
posted by queenofbithynia at 4:43 PM on January 1, 2022 [2 favorites]

I dump things rather quickly so they don't haunt me in the future. My favorite long ago second date thing was "technically I'm married but you don't have to worry about that" because I had married my BFF for university financial aid get off of parent's income statements. I also almost (at least offered) to marry another girl for a green card. I was also basically a male prostitute for a while.

I don't want my past to surprise you out of nowhere and sorta want to know your past as well. Whether that makes some sort of next-date a Yep versus a Nope is a totally different matter.

If you can't after a couple of dates blah blah blah dump dump on each other that doesn't end up in a bit of "meh don't care" you should move on. Everybody has a past that can't be changed. Is it something you judge or something you think defines the future?

They also have stories that you'll eventually know if you two stick around enough that would be better "they told me about that" than some random surprise.

Running into your SO has no relation to either of your pasts, only as much as you make it so.
posted by zengargoyle at 12:41 PM on January 2, 2022

You're probably not being asked as a test that has a right answer. More as a sort of get-to-know-you.
Also, you're relationship history is not so uncommon.

An answer might be "you know, I've never had a relationship longer than 5 months. I might like to try it someday. "

If someone has a particularly negative reaction to that, then that's a good filter for you.
posted by jander03 at 10:54 AM on January 3, 2022

I'm over 40, and my longest relationship was 4 years when I was 18. My second longest relationship was 2 years that started in my late 30s and ended about a month ago. In between, I've done some dating, had a few relationships of a couple of months each, and some first and second dates that didn't go anywhere, and some friends-with-benefits type situations.

But I like my life, and I'm not going to change it unless I'm sure the change is going to be for the better. And I also want to be in a relationship, if I'm going to be in one, with someone else who has a life they like and is not looking to remake their life around me. So I'm not getting into relationships unless I feel pretty sure about the person. Some people I date for a while and then conclude that we're not going to be able to enhance each other's lives long-term, so we break things off. I don't think any of that is a red flag. And the person I dated most recently, for two years, also didn't think it was a red flag.
posted by decathecting at 12:36 PM on January 4, 2022