Dating When You Feel Less Than


I hate being unmatched on Tinder. Hate it.  You get the little push notification of a mutual match, you swipe on it to get to your inbox annnnddd….they’re gone.  The only worse feeling is getting the match notification, giving it a few minutes to allow them the time to swipe through your photos and unmatch you, and not only do they not unmatch you but they message you. You’re in the clear right?


This happened yesterday. He messaged me immediately. I replied right back. He responded an hour later. I waited awhile then responded to him, saying I liked his bio and photos. Then…nothing. This morning I woke up to learn he’d unmatched me.

My bio includes my work info (Creator of and I link to my Instagram (which includes links to all my sites) so they could see more photos. Maybe that’s it? Or maybe it’s not? Or maybe I’m just over thinking all of this? I definitely have moments of feeling unpolished, like what I do for  a living isn’t impressive enough.

Ooh, you write a blog. How fascinating and original.  And look, you run a little website. How charming. A novel? Have you been published yet. Well, I’m sure your book is riveting! Now if you’ll excuse me, I’m the CEO of a tech start-up.  I’m very busy. 

People at the gym ask me what I  do for a living. I tell them I run a specialty events service and they say, “Do you do anything or just that?” They don’t ask it in a pointed way. I think in Manhattan being a multi-hyphenate is a thing.  Whatever the case, it leaves me with a feeling of inadequacy. I don’t lead an exciting, travel-filled life. I work seven days a week; I write; I work out 2 hours a day; I occasionally go to events to network.  I’m boring, you guise. I’m boring and unsophisticated.

On top of that, I’m not conventionally attractive. I mean, I’m pretty, but for Manhattan I am average.  Pushing fifty with wild curls and a size ten body. (Okay fine, twelve-ish is more accurate.) Nobody could ever say I lack self-awareness. that’s for sure. I am starkly aware of where I fit on the food chain. Maybe too much so. I look at photos and think, “Not bad.” Then I post them to a profile and see all my flaws: the big forehead; the thick unruly hair; the passable-but-not-great body. A lot of that, I think, is depression-related. The things I say to myself are words I wouldn’t spew at my worst enemy.  For me, there’s never a “good day” with depression, one where I feel one-hundred percent confident at all times. That rush of power – where I know beyond a shadow of  a doubt that a guy thinks I’m sexy – comes in waves.  I never allow myself to get too excited. In fact, I punish myself for doing so.  It ain’t pretty, folks.

But here’s what I don’t get: I get a fair amount of attention off-line, especially at the gym. Maybe it’s because I’m surrounded by people who share an interest of mine? Maybe it’s that they see me doing squats and deadlifts and take me more seriously? I saw a tweet in my stream last week from a dating coach that said, “Wearing make-up at the gym is not an effective dating strategy. You don’t want to be the woman who’s [sic] mascara runs faster than she does.”

You know what’s coming.


I happen to disagree. I think a woman at the gym who sweats so much her mascara smudges is sexy as fuck. But then, I’m a woman. I replied to her tweet and asked her to present a case to support that thought. No response. I’ll just say this and move on: the only people who notice (and judge) a woman wearing make-up at the gym is other women.


Look, I realize I’m forty-eight years old and therefore don’t have as many options as some other women but…I’m not ready to settle. I look at men online and go through my likes and messages and think, “These men have to be kidding. Have they seen the sun recently?” Then a stern voice intrudes and says, “Who do you think you are?” Women in my position are supposed to be grateful for what they can get, right? I don’t go for young or even younger than me guys. I don’t go for finance dudes or lawyers or anyone who works in any kind of status-associated field. I don’t (often) message or swipe right on conventionally attractive men. In other words, I stay in my lane.

This is my eternal struggle. I vacillate between feeling less than and more than enough. And I don’t know what to do about it or how much longer I can pull  it off.



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28 Responses to “Dating When You Feel Less Than”

  1. Betty Says:

    I think most people online dating go through this. And yes, I get more attention offline than online as well. But I think it has more to do with online dating essentially being a commodities exchange than a place where people seek connection. You can’t know what one is thinking. I love the Four Agreeements rule: never take anything personally. He might’ve had bad experiences with writers before. He might’ve wanted someone with lighter hair. He might’ve thought talking to you may lead to meeting you and he wasn’t ready for that. He may be married and having second thoughts about cheating. Who knows?

    • Beta Male Says:

      “Commodities exchange” is the best description for online dating I’ve ever heard.

      Unmatching is part of the normal online dating process these days. People unmatch because they didn’t look at the entire profile, figure out based on the message exchange that you aren’t compatible, one person didn’t respond to the other person’s message fast enough (that reason is surprisingly common). Ultimately, “unmatching” is more about the other person than you.

      With online dating there is a combination of the checklist mentality and the illusion of choice where people figure they have plenty of choices so they could afford to pass over someone who doesn’t fit certain characteristics. Why commit to someone you haven’t met when there is a potential date around the corner. The reality is that the brutality of the dating market is more obvious online. Personally I’m having better luck meeting potential dates at events that I enjoy going to. In fact I set up a date for next week going to one such event. Ironically if I met her online I would have passed since she has one of my “deal breakers.” However, in person I felt enough potential chemistry I am willing to take that chance despite that “deal breaker.”

  2. UWSGal Says:

    I un-match people on bumble sometimes when i realize i overlooked something that was a deal breaker in their profile. I only have 3 deal breakers and they involve children, pets and smoking and so i don’t think i am shooting for the stars here. But yeah the whole process is wasteful and should be treated as fun and window-shopping. Relying on bumble/tinder to find the one is like buying lottery tickers for income.

    • fuzzilla Says:

      Yeah, I used the lottery ticket analogy a lot to keep perspective when I was online dating. “If something comes of it – great! If not, what have I lost? Chances are I forgot even buying the damn ticket in the first place…” It could still get horribly depressing, but that helped me rein in the negative thoughts.

      • Parenting Says:

        Its depressing to hear that dating is something we all have to “get through”. I totally get sentiment and have certainly been there but Jesus what has the internet done to dating?!

        I have friends who found love on the internet but many years ago. I cant think of a single online dating marriage in the last 5 years. It seems like a suck hole of endless first dates and generally shitty behavior.

        Moxie – I dont think high powered female senior executives are doing any better in the NYC meet market than you are. Actually the are probably doing worse because most have more stringent financial demands. Dont get into your own head with this stuff.

  3. CT Says:

    Online dating makes rejection into something tangible when someone unmatches, deletes, or swipes the other way. I do not need nor want that in my life.

    I love the podcast “That’s Deep, Bro.” She (the host, a comic) talks about people trying to reach “special” status all of the time and the fallacy of that. She argues that it’s ok to be ordinary, normal, boring, even when society tells us to strive to be “special”. Most people live boring, ordinary lives, doing the best to get one foot in front of the other every single day. If you are living an authentic life and it’s enough for you, who are others to make you feel so inadequate?
    When the voice in my head tells me that I am not enough, I do my best to tell her to shut the fuck up. I remind myself that I wouldn’t talk to a friend that I love that way, so why do I talk to myself so disparagingly?

  4. AC Says:

    The only recommendation I can make is to delete the Tinder app from your phone. It’s depressing. Say what you want about OKCupid but there’s no comparison between the number of flakes on Tinder vs. OKC.

    As for the rest:

    Anyone who turns their nose up at your career isn’t worth the time of day.

    Wear what you want at the gym including make up.

    If you find yourself looking at your likes/messages and saying “you’ve got to be kidding me!” you’re not alone. I think we all though that- men and women.

    The only answer is to try and be the best version of you and keep plugging away( I know, not very profound then again neither is real life).

  5. coloratura Says:

    So what does it mean to be approaching 50 and to never have had a genuine relationship? The answers are not pretty, particularly if one has been living a full life in a metropolitan city. It is tough to be in such a situation as the proof of one’s undesirability becomes more and more undeniable as the years push on. It is an eternal struggle to find love. Don’t give up.

  6. EANx Says:

    Just FYI, men also notice the woman who wore so much makeup the sweat is ruining it. At least it’s not as bad as someone who wears a lot of perfume to work out. That’s just as bad as the person who takes up space on equipment while playing with their phone.

  7. TwoCents Says:

    Everyone settles at every single age. The difference between a 28 year old settling and a 48 year old settling is what they’re settling for. At 28, it may seem like you have the pick of the litter looks-wise, but I’ve seen people give up security or compassion or kindness for the hot woman or man. Serious personality flaws are overlooked for the “package” that has no substance. At 48, you may be settling on looks (though I don’t think that’s necessarily always the case), but you may be getting a more quality person in terms of personality and security.

    I think it only becomes settling (at 28 or 48) when a choice of partner is made based on fear. Fear of not keeping up, fear of being left out, fear of being alone. Don’t let fear be your guiding principle. And stop with the lanes and leagues. You’re grown. You’re successful. Seriously no one worth their salt still believes in lanes and leagues after 30. Sticking to that mindset and shattering your confidence because of it is what’s crushing you. I don’t disagree that dudes on these sites are looking for that unicorn, but then why are you wrapping your self-worth up in people who aren’t good enough for you because they’re still in a high school mentality?

  8. CC Says:

    Ladies, love who you are first, in every way! When you do, it makes no difference what some guy does or does not like and then if/when you find the right person, he will truly be the right person instead of someone who only likes you for the image you put forth. On top of that, if you can learn to truly love yourself and your life as you are, finding the man to fit your life becomes much less important because you realize there’s so much more to life. You only live once – do you really want to spend that life pining over someone or embracing all that life has to offer in the best way you can? Chances are, if a relationship is meant to be, it will find you when you have learned how love your own life as is. I know it’s easier said than done in the world we live in but it is so very possible.

    As for the job – whatever you do, love it and be passion about it. When I date, that’s what I want to see in a man. This may be an extreme but for example – I will be happier with a good, responsible, chivalrous trash man that is passionate about his career than I would be with a lawyer that is in it for the image. Be passionate and proud about your career whatever it is.

    Full disclosure – I’m 37 and single but I’m happy! I’ve been in several relationships and even engaged. I’m not going to settle. It’s not always easy and I still have those moments but, in general, I’ve learned how incredible life is with or without a relationship and how depressing it is to be focused on not having one. If i have anything to say about it, I’m not going to waste any time waiting on the perfect match! Life is too much fun and too short for that.

  9. Nia Says:

    I think, first, everyone can make a case that they don’t fit the mold of online dating. I don’t know where this cohort of fit, slender, fun, world travelers *are* but they are really ruining it for the rest of us!

    I recommend the TV show “Friends From College”. It really shows NYC as the very competitive lifestyle cauldron it is, and how you can have “everything” (conventional good looks, money, be married, etc) and not be happy.

    I struggle to give advice because I too feel like part of my worth or validation is feeling attractive to men. It frustrates me as a feminist that this is such a core part of my being.

    My feminist friends, who are of course average or slender body type and conventionally good looking are like “who cares!! you’re worth it no matter what!” but they haven’t had the experience of walking into a date and seeing in your dates’ eyes that you’re not “good enough”. They have *no idea* what that feels like. Whether it’s my being too tall, too full figured, my punky unnatural hair (all of which was shown clearly on my dating profiles! were they hoping I was like, way hotter IRL?), or my hippie style clothing or whatever, I was a let down for a lot of guys. It hurt.

    I don’t even know what advice to give, just commiseration.

    • UWSGal Says:

      FWIW, i am a conventionally good looking person size 4. I have had those experiences “of walking into a date and seeing in your dates’ eyes that you’re not “good enough”. If you think that any good-looking person is betting a thousand in dating, you’re very much mistaken. One difference is perhaps that I have never taken it as a verdict on my own worth.

      • UWSGal Says:

        **batting** a thousand

      • Nia Says:

        Yeah, I guess in a roundabout way I was getting at that—you can be rich, good looking, thin, etc etc and no on is immune to being judged, for sure. For me, it’s frustrating to be confronted with people, who to be fair are just trying to help, who have never been in my shoes.
        Do they still have troubles? Sure. But some things they just can’t relate to!

  10. Jack Says:

    Tinder is stupid.

  11. Bluegrass Says:

    I’m sorry to hear online dating has been frustrating you recently. However, I can totally relate. Getting unmatched is shitty and I feel like it’s almost always uncalled for. This is one reason why I’m against ghosting and such–I think that, because of the way humans evolved to socialize, such an abrupt cessation of contact often leads to a feeling of acute rejection even though not being selected for a date is almost never a big deal at all. Now people can make pragmatic arguments for just cutting off contact, and saying that it saves time. But I feel like the same thing could be said for real-life interactions. If you are on the phone with your friend and need to go, why not just hang up as soon as you want? In theory, your friend will get the picture and they can just finish telling you whatever later. But, because we evolved to live and depend on each other in relatively small groups, such an abrupt interaction in real life would probably indicate that some shunning was about to go down, and so would be alarming.

    I recently had an unpleasant interaction myself with someone blocking me via text. This guy and I seemed to be hitting it off and I asked him to text me, which he did. So we chatted some and again, seemed to be getting along quite well. We agreed to meet up sometime the next week. Well yesterday I texted him and asked him how his weekend was. Bam, blocked. To be honest; I found it quite hurtful. The thing is, I never give much of a shit if someone I just met who I thought was interested in meeting up ends up not wanting to meet. But the feeling of being blocked hurts. It seems like a rather extreme way of avoiding having a very small interaction where someone could just say that they’re really busy for the foreseeable future, or that they’re going through some stuff that they need to sort out. And then I’ll take a hint, and if they want to re-establish contact they can get back in touch. But I don’t feel like I did anything to the guy that warranted getting blocked.

    I just feel like online dating interactions too often are needlessly disrespectful of other people’s humanity. I realize there are cases where silence is fine–especially if you haven’t spoken with the other person much. But if you’ve exchanged messages for a while and made it look like you want to meet, why not give the person the courtesy of saying that you’re not feeling up to it anymore? I mean, I am often very nervous or apathetic about meeting people that I’m attracted to and are out of my league, I certainly wouldn’t begrudge someone not feeling up to meeting. But when they just stop responding it makes me feel like maybe something happened to them (very unlikely, but that’s the optics of it) or that they just deemed you unworthy of an even courteous wrapping up of your conversation. That whiplash of “oh maybe this will be fun, this guy seems nice” to “this guy is a cold fish who thinks it’s great to just stop messaging someone whenever their interest to them has expired without so much the kindness of a goodbye” is jarring and, I think, probably the worst part of online dating. Oh well, it does seem that a small proportion of people recognize that it’s not nice.

  12. 40something Says:


    I think you are a lovely lady. Curly hair rules. I’m never really certain what “conventionally” good looking translates into but I’ve been called that. However, I have a self deprecating sense of humor and admittedly refer to myself as a declining commodity.

    I admit I only did online dating for a couple of months so I don’t have much to speak of other than what I’ve seen. I do think the key is not “settling” for someone who doesn’t have the same major life goals (marriage, kids, etc) because I believe that only will leave one resentful. There is compromise and then there is feeling like you give up what you want -2 diffy things.

    Everyone has a different concept of what they find attractive. At this point in life, I have found it to be more difficult where the feeling was mutual.

  13. AnnieNonymous Says:

    I don’t think it’s about looks as much as you think. It’s my experience that the beautiful women go through long stretches of being single and only getting asked out by entitled jerks. Nice, normal guys assume they don’t have a chance so they don’t bother. Beauty privilege only goes so far…attractive women may be offered some desirable things, but the people offering those things usually except something steep in exchange. Just look at the women of Fox News. They were rewarded for their looks but the tradeoff was appalling. And look at Joan Holloway. She was the only one who was single in the end. Men offered her things, but not the things she actually wanted. On my own micro level, my friends who are more in the middle of the looks spectrum get openly hit on more than the ones who are beautiful. They’re just more approachable.

    Ever think that you don’t get approached because you’re much more attractive than you think you are? Go through your past posts and count the comments from men stating that they never ask out the truly beautiful women because they presume that the women must have gaping personality flaws. It’s proof, right here on your own site, from the men who insist that beautiful women shouldn’t struggle in dating even while those men are uniformly deeming those women undateable without speaking to them. Start saying you’re an event planner. Go to the gym at 6 or 7, when the guys with normal jobs (and life expectations) are hitting the gym. If you’re going to the gym more toward the middle of the day, you’re encountering men with weird schedules and dumb dreams of hitting it big with a stupid scheme. They’re multi-hyphenates because they haven’t actually followed through on any of those plans yet, and because they have to have 3 jobs because they refuse to work normal hours.

  14. Noquay Says:

    Went back on line for the first time in 3 yrs after a rship overlapped me with another and I immediately went NC. Like a previous commenter, I am a size 2-4, an athlete, very well educated and high earning for the region supposedly exotic due to my mixed race heritage. Was on 5 sites, now down to two and it’s an utter suck fest. Used to be that living in my small mountain town wasn’t an obstacle but now guys want womenwithin 5-10 miles of them even though they’re willing to travel 100+ miles one way to recreate. Overrode the normal “match” feature on Match and searched myself and there’s frankly very few guys in even remotely attracted to; same deal on Fitness Singles; very few actually fit men. I know there’s attractive, high functioning men out there as a good many are here now for the 100 bike race but just not on line. The only upside of this adventure is meeting a coupla guys who became good friends; one, a guy that doesn’t want to drive this far and another very into me but I’m not at all attracted to him. I think it’s a s$&@fest everywhere now. Will be leaving come Spring and looking for cool outdoor towns where I can meet fit, older, guys IRL.

    • Nia Says:

      If you’re looking for a town full of fit people and you’re in Colorado, Denver may be your landing zone. I am in Denver and I struggled to feel comfortable with the high, almost overly intense focus on fitness, sports, endurance and obstacle races, and outdoor recreation. (I even wrote a letter to this column about it!)
      Denver has a *lot* of very fit men who *really* care about both their own fitness and the fitness of their partner. I live about 10 minutes from arguably the wealthiest area of town in Denver proper (so, excluding very high net worth outlying regions) and everywhere you look are very handsome, fit older men who at least to my eyes, appear healthy, employed, and normal.

      Denver also has a very active social scene—many bars, clubs, restaurants, cultural events, and the like. Its proximity to the mountains as well as other outdoor features (undeveloped areas, rivers, etc) means that if you like to do races, camping, hiking, kayaking, ski-ing and so on, you’re in hog heaven here.

      The downside is…

      It’s very pricey, the housing market is super hot right now, and its a boom town, so almost everywhere is crowded. Traffic is hell.

      The other downside is that, and this is more subtle, that the town is made up mostly of transplants who moved here out of desire, (so, not for family, work, or health reasons). Those who move to a town to have “fun”, either to smoke weed legally, to have outdoor fun, or to be in a happening, hip town, often lack maturity, selflessness, and self awareness, which are really key qualities in a good relationship.

      I have also found that many men have a quality of really REALLY wanting to move to “Wagon Wheel, CO” (my made up crappy little mountain town, pop 150), to get away from it all, get back to nature, not be held accountable to social standards, to live a very simple, stripped down life, and to be able to do whatever they want (fire weapons in the air, race 4 wheelers, drink all day, have huge campfires, or whatever). These type of men are often really antisocial and struggle with really connecting (as you no doubt found in your own small mountain town!). Denver is a compromise for them, their plan is to get a woman and then move to Wagon Wheel *forever*.

      So, there’s good and bad :)

      • Jack Says:

        Oh yeah, I have that fantasy of moving to the mountain town to get away, though as an East Coaster I’m thinking Maine or New Hampshire. Of course you do need to feed yourself and buy essentials/guns/toys so unless you hunt your own food that fantasy only goes so far. But as a second home getaway could be nice.

  15. Pina Says:

    I’ve said it before, you would be greatly helped by studying compassion. Self-compassion has been shown to be far more effective than trying to build self-esteem. Have more compassion for you and more compassion for others and your life will change for the better in tremendous ways. there are several books and recordings on this in Buddhist study and in the self-help section of bookstores/ libraries. You will be glad you checked it out.

  16. David Says:

    Five years and eight years back, I vividly remember two instances of women in the gym who wore body tights that left little to the imagination. They also sweated profusely when they were working out, including around the crotch area and the crack around the ass. Both times, I could clearly sense the rest of the women in the gym were not keen about these women.

    Do you think they were clueless about how revealing their outfits were to their sweating? Of course not! For the guys, it was sexy as hell. One was a perpetual guy magnet. The other was a little intimidating with her confidence and amazing body, but that was a good filter to make sure the sexy confident guys approach her. It works. I still vivdily remember them and it still gives me a hard-on being reminded of it.

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