How Do You Find a Man When You’re an Unconventional Woman?

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A last-minute trip to the gym Friday night resulted in me being invited to join an interval running group of other members. I gave the guy – who looked to be in his mid-thirties – my number so he could send me all the details. As I suspected, he used the opportunity to text me and ask me out. “I’m flattered,” I said. “But I prefer not to mix gym business with pleasure. Hope you understand.”

Now, if I had found him attractive, I totally would have said yes. I normally work out in the mornings. He works a traditional 9 to 5 job. The chances of us bumping into each other are slim. He said he understood but I still felt like shit. (He never sent the info for the interval group, so I don’t feel that bad. I  found it myself on Meetup.) I knew why he was asking for my number. I should have taken his number and followed up. I think giving him my number sent a mixed message.

As a result of this interaction, I started to consider the possibility of opening myself up to dating men in their mid-thirties. I say dating because – let’s be honest – a relationship like that is unlikely to turn serious. I know this. But I also know that I get a fair amount of attention from men in that age range. So why not go for men that actually show interest?

There are downsides to this, of course. All of these relationships would be temporary. I’d invest time into something that probably wouldn’t result in more than a casual two to three-month fling, if that. And then there’s the fact that I’ll have to weed through a fair amount of bucket listers and immature men who have bought into the myth that “older” women are dying to find a young stud they could trot out like a prized pony, something they learned from their male counterparts. From my limited research, most women my age can’t be bothered with anyone considerably younger. I wrinkle my nose in disgust when I think about sex with a twenty-something. I have no interest. Thirty-five would be my limit. I once had a man who was that age ask me the tried and true “Are you into younger guys?” question.

“Why?” I asked. “Do you know one? You’re pushing forty, dude. Your days of being a ‘younger guy’ are behind you.”

There’s a part of me that feels rather pathetic for branching out like this, but the alternative is just as unattractive. I can’t keep going for men my age and older just to be rejected. It’s too soul-crushing. Not to mention – and I’ll get shit for this – many men my age do not take care of themselves. The more fit I become, the more I notice men my age who aren’t. Many of the men online in their forties are slobs. Tinder is a dumpster fire of haggard looking dudes. Bumble is useless at this point due to all of the fake male profiles. And before any guy says, “But that’s just your experience!”, I’ll tell you you’re wrong. Because of Bumble’s business model, where women initiate communication after a match is made, men quickly lose patience with the app because women don’t reach out. More men abandon the app sooner than women do, leaving a database full of dormant profiles. So, while I’ll use online dating and apps because that’s where the people are, I think the majority of my focus will be offline methods.

I find myself wanting to get out more and be around people. I joined a few Fitness-related Meetups, but was disheartened to see that I was one of the few “older” members. I suppose I could start a fitness group for 35+ members, but I know it will end up being mostly women that join. The idea of meeting men offline is looking more and more favorable to me. Something about me is more open these days. I’m being approached more. Besides believing that online dating and dating apps are now an exercise in futility, it seems like every week there’s a new story about a man using these platforms to exorcise his rage at women. Take this latest story for example:

‘You are one fat mother f***er’: Tinder user purposely swipes right to a woman on the app just so he can body shame her and tell her to ‘stay in her league’ in a series of rude messages

What is happening to society? How many stories like this have we heard lately? I’m convinced apps like Tinder are full of people (men and women) who are so banged up from the dating process that all they can do is lash out. Sure, some women jump out of the gate with questions about what a man does for a living. That’s obnoxious. But I have yet to see a case of a woman being this intentionally malicious.

As it turns out, somebody stole the photo of a conventionally good-looking guy so they could match with women on Tinder and just to tell the women how disgusting they are. I say “conventionally good-looking” because he fits a mold. I’ve come to believe that it’s those men and women – the conventional ones with conventional looks and conventional jobs – are the ones with the most success with these online dating methods.

My physical presentation is not considered conventional. I am a size 10 with wild curls. The curly hair alone often gets me passed over.  Then there’s the fact that I don’t work a regular job. If I say I run a small business, well, I must be supported by Mommy and Daddy. I couldn’t possibly actually run a six-figure generating business that supports me.  Oh, and don’t forget that I’m 48 and never been married and don’t have kids. That last one – the lack of children – is usually read as “defective” in some way. Not ever being married is bad enough, but no kids? There has to be something wrong with me.

And you know what? There are things about me that are defective. I don’t deny that, but I also don’t define myself by those experiences. Unfortunately, as a woman, many people take it upon themselves to label me because it’s inconceivable that I could be messy and complex and broken and resilient and caring. Nope. We don’t get to be all those things.

I feel like it’s a constant uphill battle to try to meet someone. I’m almost 50 but don’t look my age. (I know. We hear that all the time.  I know.) I’m not widely considered conventionally attractive. I’m into fitness. I don’t work a regular job. I’m an internet writer with a  strident demeanor. All these things work against me. I’ve chosen a path that for a man is socially acceptable, but for a woman is taboo.

So it only seems appropriate that –  like every other aspect of my life –  I choose the road less traveled, so to speak, by going against the grain.




  1. There is a woman at work, conventually attractive, smart, into fitness. Capricorn. Unlucky in love. She comes up with many reasons why, but she has a blind spot — she’s very judgemental. It puts a barrier between herself and everyone she meets, and she can’t accept that her judgemental (accompanied by dismissive) attitude has much to do about love-luck-lessness.

    I think each of us are aware we have blind spots to those parts of our personality that deter love, but remain unaware of how crippling these may be. Instead, we tend to attribute misfortune to items we better understand about ourselves. Lack of Height, money, beauty – everyday we see examples of people who overcome these types of “negative” attributes. It seems these obvious maladies aren’t keeping them from finding a mate.


      1. I agree on the hair as something that guys pass over, and I have NO idea why. My hair is naturally ringlet curly. I used to wear it curly sometimes, flat ironed sometimes. When I got divorced and went back into the dating world, I was trying to figure out what worked and what didn’t to garner attention based on my looks and style – I could wear the same outfit to bar, gym, mall, etc. If my hair was straight, even in a ponytail at the gym? I’d turn heads. Curly? No one noticed me. I did my own little experiment over and over and same results, every time. I don’t get it. But now I wear my hair straight most of the time – or at least when I’m out and hoping for some attention.


        1. I agree on the hair as something that guys pass over, and I have NO idea why.

          Oh, I can answer that for you. Racism. Curly hair is not considered a characteristic of a white person. That’s why I get offended when people suggest I straighten my hair, as what they’re really saying is, “You should try to look more white.”

          I was watching a documentary about Italian immigrants not too long ago. When we immigrated here, we were classified as “non-white.” If we settled in the south, we were marked Black on the Census and subjected to segregation laws. We were assumed to be of mix race because of our olive complexion, facial features, and hair.

          Awhile after we came here, many Italians married white people with with more traditional attributes like fair skin and straight hair, thus lightening our complexion. There’s along history of disregard for Italians, as people from Italy and Sicily were considered “dirty.” My father was called a dirty guinea more times that he cared to remember, and was passed over for a promotion to Superintendent of our town’s school system after working as Assistant Superintendent for several years and after having experience in literally EVERY facet of education. Who got the job? Oh, a nice Irish boy with pasty white skin and red hair who had half my father’s experience.

          I want to be sure to state that I am IN NO WAY trying to imply that we suffered from the same levels of racism and hatred that people of color did. Not even close. Comments about my hair are obnoxious and inappropriate, but easier to shirk because there isn’t the same history attached to my hair. Comments about the hair of a person of color are usually racially charged indictments that go beyond the aesthetic.

          When people look at someone with curly hair, it is often assumed that person is of mixed race or not white. That’s what is behind it. Good ol’ fashioned prejudice and racism. People will disagree, but that’s only because they’ve been conditioned to believe otherwise, forgetting where the idea that straight was better came from.


          1. Interestingly, now that my hair is blonde, I get more attention when I curl it. I guess the bottom line is that women can’t win, ever. However you have a body — ur doin’ it wrong.


          2. Very well stated Moxie.

            I’m black and I’ve noticed this as well. I do not straighten my hair for th same reasons you highlight but I do wear long braids on occasion. When I do I notice I get more attention from (non black) guys than when it’s in an afro texture. The braids flow downward, approximating straight flowing hair to a certain degree, and probably looks more “acceptable” than an Afro puff.

            My ex was a very handsome Italian-American. He went to a mostly white (literally there was only one Asian family) private school growing up and told me the other students would poke fun at how dark he got when outside and “jokingly” pointed out his heritage in what I considered a derogatory way. He brushed it off but I know there was something more to it than kids messing around. IDK, being black I don’t really take those kind of comments at face value.


  2. I think women without kids are badass! My immediate association is that she’s a woman who knows her own mind and didn’t fall for the indoctrination of child=fulfillment.
    I love your site and with my go-to online communities going defunct (the hairpin, the toast…not xo) I’m hungry for woman’s writing that’s unique and not just humble-braggy and generic. Keep it up, all of it! I look forward to your book. You might be interested in Nicole at The Billfold’s experience with self publishing her trilogy. She breaks down costs and gets into the nitty-gritty of it all.


  3. When we’re talking about 35+, younger is kind of irrelevant I think! Granted, I might be biased because it’s the same age spread between me and my boyfriend, but everyone involved is a fully-functioning adult with plenty of life experience, so I say go for it. You look amazing, you feel amazing and there’s no reason to limit yourself from where I’m sitting. Btw, how adorable that a 40 year-old man would refer to himself as a “younger guy”!


    1. Alone and celibate?

      Certainly singke, which is not the same as alone. But celibate? Clearly getting laid isnt the issue. It is finding a relationship.


  4. One of the things I hate most about dating conversations is the way people accuse me of shooting down good options. “Why don’t you join a gym? Take a class? Go to that new open mic?” When you answer along the lines of, “I’ve already done that and it happened to not work out for me. I’d like to try something new instead of persisting in doing something that hasn’t worked,” people act like you’re being difficult. They don’t know what it’s like to have a decade-long backlog of having tried out all the easy options already.

    I guess what I’m saying is that you don’t need to force yourself to find someone at the gym or another fitness activity if that’s just not how things are shaking out for you. For what it’s worth, you don’t need to feel any kind of way about rejecting that guy. He’s using his presence at the gym to try and meet women, you turned him down, no harm no foul.


    1. **When you answer along the lines of, “I’ve already done that and it happened to not work out for me. I’d like to try something new instead of persisting in doing something that hasn’t worked,” people act like you’re being difficult.**

      I find that to be true no matter what the topic (i.e., not just love life).


      1. That’s definitely true. People are so defensive when your answer is basically, “That brilliant idea you just had? I had it five years ago and I tried it already.”


        1. I mean, if they just don’t know what you’ve tried and are genuinely trying to be helpful, then fine, I guess. It’s the “act like you’re being difficult when you say you’ve already tried that” part that makes me stabby – it shows they’re not actually listening and just like hearing the sound of their own voice.


  5. I’m all for more “offline” dating, Moxie. I’m a 50-year-old woman who has been using online dating for two years now. Yep, late to the game after the end of a horrible long-term relationship. Online dating gave me more confidence in my ability to attract men in general, which I was doubting as a middle-age, plus-sized woman. However, online dating has never resulted in anything more than two or three dates with any one guy. Online matching just doesn’t seem to be an effective way of determining in-person chemistry – at least not for me. During that same time period, I’ve had non-monogamous, steady relationships with three men I met “offline” where the chemistry was instantaneous. It felt easy and natural, inexplicably different than online matching. As for the age thing, I’d say don’t put too much thought into it but don’t expect too much of younger men. The gentlemen I’m dating are age 64, 40 and 35. The older man and I have more of a traditional and intimate, albeit open, relationship. If we lived in the same city, we might be more serious. The two younger ones are, frankly, more about having regular, casual sex, and the occasional shared meal. They are respectful relationships but will never result in a long-term romance.

    As for the story about the Tinder asshole, I don’t think that’s too common. I’ve been fortunate to have only man directly insult me about my weight. His comment : “You look like someone who’s never late for dinner – especially if someone else is paying.” I could have let it go but I put him on blast. The bullies are emboldened by our silence.


    1. I think bullies are looking for a reaction. I have nothing against blasting them, but maybe they are best ignored? That abusive guy on Tinder? It was obvious to me that his profile photo was fake. Given the poor English, I suspect that he’s a just a frustrated scammer, maybe from another country. Scammers should always be reported to the admin.


  6. How do you find a man when you are an unconventional woman? Reading this post, it appears as though the answer is that you don’t. Woman in her 40’s, never married, no children, rejected by men her age or older for serious relationships and thus has to settle for short term casual relationships with younger men, otherwise said woman is alone and celibate. This is depressing.


    1. I don’t think it’s that bleak. What Moxie is discovering about herself is generally true. As she becomes more open and confident, especially in an environment in which she is happy and comfortable, she becomes more approachable and more attractive. I don’t think she (or I) is doomed to either celibacy or a lifetime of short-term casual relationships with younger men. Live your life, be happy and you will draw more happiness into your circle, whatever form it takes.

      Liked by 1 person

  7. Hmmm, I have a couple of very attractive friends with exotic looks and long, dark curly hair, who always got a lot of male attention when they were single. Still another has curly red hair, same deal. Many men are definitely into the unconventional look. As far as dating guys a few years younger, so what? Most men have no idea how old you are, they just find you attractive. If 35 is your limit, that sounds reasonable to me. They are certainly more available younger men than older men, so why limit yourself?


  8. Wow, I really feel you.
    I’m a “brainiac”–a voracious reader, and an offbeat person (I collect 60’s crewel work and throw theme parties for perfumes, among other quirks). I’m tall and I’m carrying a few extra pounds. I’m also an INTJ *and* an Aquarius, the rarest female Myers Briggs type and the weirdo of the zodiac, for good measure, hee.
    I’m weird. I was raised on a commune and march to the beat of my own tuba weird.
    Yeah, finding guys was/is hard. I feel like there is no answer–it’s going to be different for everyone. I have had love of all kinds—everything from one night stands to engagements and I still somehow feel like I “never got guys”. There’s a story in our society about unusual women and how hard it is for them to find men–but you see very odd people together all the time!
    Maybe it’s not the weirdness of the woman, it’s just…being different leads to different choices: no kids, never married, living alone, entrepreneurship. So while “normal” people are doing stuff like oh hell I have no idea—going to “the club” or something? Weirdos are starting their own businesses, forging their own path, and staying free of the stumbling blocks of the rest of the world.
    So…the path you chose just doesn’t have those legions of men all over it. But I believe it will lead you to one.
    It’s luck. It’s timing. It’s doing the work on yourself and going through those nights of the soul and just hoping, never losing hope.
    I really hope you find someone. I’m puling for you.


  9. I was lucky to have had kids at 25 and 27. I now realize that having children and a relationship are two different things. I divorced my ex at 30 and was glad to date and have some wild flings again. I am 32 now. I am sure that I would be frustrated to no end if I was trying to date and think about starting a family with that potential someone if I was still single and childless at this age.

    But finding a long term relationship online or on some app has been frustrating to say the least. I have met and dated my share of douchebags, jerks and also nice guys that just don’t turn me on. As for meeting people in real life, it’s hard to find the time with kids and a full time job. At this point, I am happy with my family and my career.

    But I still need sex. I have a high sex drive. It’s not hard finding suitors if I state that I am seeking NSA sex. Guys in their 20s are a joke. They talk a lot of bluster. Guys in their early 30s are somewhat more presentable. But they don’t have that social confidence to come across authentic. I find that mid to late 30s works for me. After searching for four months I found a guy. I did it at my pace, fully aware that there would be all kinds of jerks. I just didn’t let them get to me. This guy and I hit it off. We had my fantasy which was to spend the weekend in bed with red wine. We planned to do it again the next time my kids were away with my ex. But he flaked out. If he wasn’t going to be respectful with my time, I won’t wait for him. I cut him off. Sure I was angry but I have no time for losers. I won’t let it get to me. I’m still looking for someone else for round two. It takes time and I do know that this might take time away from finding a real partner. I’m doing this now because I am realistic that few guys would be interested in the baggage of a 30something single parent with two kids.


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