Give me your feedback / experiences / advice!

I turn 31 this year and never had much luck dating in life, but most of it being women never older than myself.

Are older woman more serious about genuine relationship, a future and more into sensual sex? Anyone find an amazing single mom?

I feel like there would be a lot less drama if I dated on the older side but I’m curious.

22 comments
  1. I think the women your age notice the ticking of their clock. There comes the panic of no longer binding a guy permanently to himself.

    So they have lower demands. However, they are no longer so crisp.

  2. I was 42 when I started dating again… it was an interesting experience. I mostly dated women in their mid-to-late 30s (I have/had nothing in common with 20-somethings).

    I most often ran into two types: women who wanted to get pregnant *right now* and the walking wounded. The former was a non-starter for me. The latter were women who had been jerked around badly by exes and then again by online dating. They were usually single mothers, which wasn’t a deal breaker for me. The issue there was that they all approached dating like a police interrogation. I had more than one woman open a conversation by asking “so what’s *wrong* with you?”

    I did eventually meet someone great. We’ve been together 4 years and recently got married. She has two kids, who are both fantastic. We took things slow at first and just let things flow. It’s been low drama and the physical part is off the charts.

    The thing to understand with single moms is that, if things get serious, you’re also in a relationship with the kids. If things don’t click with them too, it’s not going to last.

  3. It’s pretty easy to meet women and get dates, but it’s tough to find a meaningful connection. Basically, it’s – pretty, emotionally available, no kids: pick two. The women that remain single into their mid 30s usually either focused on their careers and have trouble connecting with men or they have kids. So you’re either dealing with someone pretty and fun but incapable of emotional intimacy, or a single mom who’s free every other weekend when dad has the kids and she’ll spend half the weekend complaining about what an asshole he is.

  4. Women will probably come with baggage, ie good reason they are single (from career focused to bad news) or from broken past relationships / marriage and possibly with children.

    As a 35 year old, you can probably still connect well with people +/- 5 years, so dont box yourself in. HHowever, do be willing to compromise and realise you are not perfect either and people may be compromising for you.

    The older you get, I think the more important capital is. People may own homes and will want to cohabit with people that can share the cost. If you come empty handed, with no savings or a home, that is a red flag. Not a deal breaker but something to question

  5. Turn 40 next year.

    From 2019-2021 it was actually pretty good. Once I got my profile tuned up so it marketed to what the women in my city were looking for, I got plenty of matches and was getting dates. Covid hit, and it became a sort of ‘siege mentality’, dating-wise, so I was actually getting a lot more dates and a lot of fucking during that time.

    Then I met a great one in the spring of 2021, who I thought might have finally been my One, only to leave her when I moved halfway across the country to pursue my career. Career is number one in my life, and it’s silly to expect a woman I’ve barely dated for 6 months to move with me.

    Since then, though, it’s been really dry and frustrating. New (way smaller) city with small town stuff: everybody is already married, or if they’re single it’s single with a kid, small gene pool so they’re not as attractive (and actually pretty overweight), or they’re really seriously fucked up mentally. It’s been great for my career, but shitty for my social and love life.

    Dating (so far) in my life was best from about 33 to 38. Once you get past that, the pool dries exponentially, and you start to realize that everybody who’s left (yourself included), who has never been married, is probably single for a good reason like they’re just not good enough, or have some personality disorder, or disability, or something. Dating past about 38 has been the equivalent of rummaging through the discount bin, ‘slightly damaged’ shelf and cast-offs/returns at the store.

    Make of that what you will.

  6. Just as badly as the 35- dating scene. But then again I never tried dating older women. Nor would I ever date a single mom. Regardless, dating was just as unsuccesful for me over 35 as under 35. I solved this little dilemma for myself by quitting dating altogether.

  7. I’m 38 and never been on a date or in a relationship, and I actively searched for someone for over 20 years with nothing. For me, years of rejection and stuff like that made me stop caring.

    While asking in person, the best thing someone can tell me is no. About 80-90% of the time, I would get disgusted responses, been laughed at, been ignored, etc. What made me finally stop caring was when I was talking to a woman for about an hour at a local game store who told me she was single. When the store was closing up, I asked her if she wanted to exchange contact info. She said “oh”, took out her phone, took my picture and left. About a week or so later, an employee at that store showed me that she geo tagged that picture on a “losers who asked me out” Instagram page.

    That was the final straw for me that made me finally stop caring about trying to find someone.

    Leading up to that, I was on dating sites for almost 17 years with zero response messages and no matches even with a year and a half of premium on them. Yes I had my profiles and the way I messaged people looked at by dating coaches and they said they looked great and didn’t know why I wasn’t getting anywhere. I was on Plenty of Fish and OkCupid from 2003 to January 2020 and those were the two I got the year of premium on in the summer of 2018, and I deleted all of my dating profiles when that ran out. I was also on Tinder for about 6 years with no matches, and I was on Bumble and Hinge for about a year, and I stopped using them because 99% of the suggestions I got was the first day or so and I slowly stopped getting suggested profiles, and I ended getting one or two new suggestions a week.

    I tried clubs for hobbies and sites like meet up, but when ever I check, there are no groups in my area that match the hobbies I’m looking for, and for the ones I want to try, they start when I’m at work and will end by the time I would get off and try to get there.

    I know I’m not perfect, but I know my women friends told me the way I talk to women looked great and I couldn’t see why I wasn’t going anywhere. The same thing with dating coaches. I went to 3-4 dating coaches as well. There were maybe one or two things I could say differently, but each one shadowed me on trying to pick up someone, but they told me overall they didn’t know why I wasn’t picking anyone up as well.

    All that made me realize I shouldn’t try any more. Nowadays, if you come to me and tell me that a perfect 10 who matches my hobbies and interests, I would think you’re trolling with me and would tell you I’m “busy” playing video games or doing one of my hobbies.

  8. You are moving into your prime dating years just as the women your age are moving out of it. Watch out for those deciding to lock you down as their biological clock is ticking louder each year.

    There’s no rush. Time is now on your side.

  9. I don’t even try to date. I have nothing to offer a woman. I make enough money just for me, I prefer to be alone most of the time and to solo travel. Sure, I’m a good conversationalist, good writer and artist, but that doesn’t get a guy laid these days.

  10. The last time I was single I was 32. I was regularly approached by 22-26yos when I would go out.

    For a while I wrote them off entirely and focused on women more my own age. Every time I went on a date with a woman my age or older, it felt like a job interview. Everything felt so serious and it totally lacked that mischievous flirty vibe that I would get with girls in their 20s. Older women also seemed to gossip and talk shit waay more, too…

    Ultimately started dating a 25yo and we are still together 5yrs later.

  11. From extensive gossip with the guys at work and observation of the women, its “sane, hot, no kids, you only get to pick one”. With a hilarious side dish of sometimes you’ll find out later that she’s not as single or as childless as she initially implied, LOL. I might forget to mention I keep tropical fish as a pet, but its a whole nother ballgame when she drops the news she “technically still has a husband although they’re planning to separate” or “I forgot to mention my three year old toddler”. I’ve heard crazy stories at work…

    Note that’s getting so old that some of the “early start” single moms no longer have their kids around their neck, their kids are late teens or college age if she had them when she was in high school, so you don’t have expensive baby sitter drama or you’re not my dad drama if the kids are literally living in a college dorm hundreds of miles away, at least “most” of the year. On the other hand some of the no-kids women hear the clock ticking and their egg carton is almost empty so when they say “oh don’t worry about wearing a condom” that is precisely when you most need to wear a condom, LOL.

    Aside the the child drama above, women generally do NOT get less dramatic with age, unless you’re dating senior citizens, so you’re better off with a younger one. An extra five years of being single and unable to marry anyone isn’t going to make her any more sane.

  12. 36M. It isn’t bad for me I have a few dealbreakers and am open to much more than most it seems.

    1) I do find that *many* women this age have a chip on their shoulder. They have this thought process that I may be like their Ex, and therefore I should be treated as if I *will* be like their ex. I generally confront them about this thought process.

    2) Lot of divorced/separated women. I don’t mess with women that aren’t fully divorced, don’t care how far along the proceedings you are. This caused one girl to lash out because I was ‘missing out on a great woman’.

    3) Something like 75% of them have kids or want them right fucking now. I am childfree, and have a vasectomy. So this is a dealbreaker. I might need to loosen this a *little* and be OK with kids that are not in the house (18+). I have met some great women that were already mothers. My last Ex was actually, shes the *only* mom I ever stayed with. No baby daddy drama, shared custody was worked out, she was kind, generous and caring. They exist, but I will say they are rare as fuck. Most I’ve run into tend to look for step daddies to help with their kids.

    4) The sex isn’t bad, and some are pretty great at some stuff. I find a lot of them (especially divorced ones) have explored things and generally know exactly what they are cool/not cool with. So if you want to try something new, be prepared for the ‘tried once didn’t like’ and the conversation ending. If you are already sexually experienced this shouldn’t be a problem though. Some already have their Tubes tied, or otherwise cant get pregnant so thats a bonus. Lot of them are OK with just shoot and scoot if the attraction is there.

    5) I wouldn’t say that they are more serious about relationships in all cases. Some are still in their ‘party girl’ phase. Some still feel the need to keep men at a distance because one did them wrong. Some still feel that their career is more important than a relationship. Some put silly ‘checklists’ that must be met before things become serious.

    6) People in this age bracket have settled into life. They generally have their own place (some still rent, others own their house) a car, etc. The usually don’t want to change what they are doing/how they live (myself included) so it does make it difficult to navigate sometimes.

    7) Drama doesn’t seem to be any less or more common. But that can depend on what you think drama is. Women that like drama, will seek it. Those that don’t will avoid it.

  13. The most fun I had was dating single mothers who shared custody every 2 weeks or so. In a nutshell, available only every other weekend or so. The intensity will build and then you are gonna have an awesome time with her.

  14. I got out of a shitty marriage in my late 40’s and dating was fucking awesome.

    Before I found the woman of my dreams, I was getting laid multiple times a week.

    A few times, I got laid twice in the same day, by different women.

    Sure beat the hell out of when I was an idiot in college practicing serial monogamy.

  15. 10 years ago when I was 35 and dating. It was miserable.

    Over the course of a year on OkCupid. I met ~80 woman.
    Had second dates with 4.
    Third dates with 3.
    And Four+ dates with 2.

    One of those women is now my wife and we are very happy, but I can’t say it was a good time.

  16. Not well. In my experience, what woman expect from you increases ten fold and not many hold themselves to even close the same standards.

Leave a Reply
You May Also Like