Tips for dating with "niche looks" in my 40s

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:FFS- People should read before typing comments based on incorrect info shared by OP. He said that he did NOT sleep with the trans women he inadvertently dated, and that he gracefully exited those situations. My DH shared a story of when a woman he was meeting for a pool game at a fashionable bar turned out to be a man. Like OP, he was nice about it but got out as quickly as possible. That is what well-adjusted hetero men do.

How does a person who isn't actively looking for such end up "inadvertently" dating multiple trans women? I think you forgot to turn your brain on today.

DP.

Because some people wait until they are into you to reveal they are trans. I have met a few trabs women, and sometimes, you can't tell. I am a woman. I imagine men are even more clueless.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:FFS- People should read before typing comments based on incorrect info shared by OP. He said that he did NOT sleep with the trans women he inadvertently dated, and that he gracefully exited those situations. My DH shared a story of when a woman he was meeting for a pool game at a fashionable bar turned out to be a man. Like OP, he was nice about it but got out as quickly as possible. That is what well-adjusted hetero men do.

How does a person who isn't actively looking for such end up "inadvertently" dating multiple trans women? I think you forgot to turn your brain on today.

DP.

Because some people wait until they are into you to reveal they are trans. I have met a few trabs women, and sometimes, you can't tell. I am a woman. I imagine men are even more clueless.

You do realize how rare trans women are in the wild and how even more rare the ones who have no obvious male traits are? OP might as well buy a lottery ticket if his story is remotely true. You can believe him if you need to though.

Fair enough, but it depends on the crowd. Trans women may be few, but they may be concentrated in particular cities and careers. I never knew any until law school, and then I met two in my law school class.

[Anonymous]

Anonymous wrote:Um. There are lots of trans women who are way hotter looking women than those of us born with vaginas. And with online dating, you aren't going to be in contact with their friends and family before the date, so you have no source/context for knowing that they transitioned as you would if this were someone you met IRL.

See, this is why OP is so seemingly in the dark. His female friends are too nice and too woke to tell him the truth.

[Anonymous]

Just my personal preference but if you didn’t have so many tattoos you wouldn’t be on this forum asking us this question.

Wink wink

[Anonymous]

OP here, addressing the various comments:

PP was correct, dating was broken off prior to becoming intimate. By "a few" I mean two. I figured that with me looking so "alternative" and being in that scene in a few aspects is what may have attracted them to me. If I come across a profile that is clear in that regard, I'm swiping in the negative. Wasn't aware that going on a couple dates with someone that you are unaware is trans puts you on the "queer spectrum" but here we are I suppose.

Not going to get my tattoos lasered off as 1) I like them; 2) That would take years; 3) That would be excessively expensive 4) I like them.

Yes, realize that I am short but short (heh) of surgery there isn't too much I can do there.

Enhanced women comment: That is wild. Those brainworms are burrowed deep.

Yep, friends are too woke. That is the issue.

Update on date: Went and grabbed tea, no walk. Chatted for a few hours. She has a good sense of humor and great taste in music. Planning on a second date to go shopping for records/vinyl and grabbing brunch.

[Anonymous]

Anonymous wrote:OP here, addressing the various comments:

PP was correct, dating was broken off prior to becoming intimate. By "a few" I mean two. I figured that with me looking so "alternative" and being in that scene in a few aspects is what may have attracted them to me. If I come across a profile that is clear in that regard, I'm swiping in the negative. Wasn't aware that going on a couple dates with someone that you are unaware is trans puts you on the "queer spectrum" but here we are I suppose.

Not going to get my tattoos lasered off as 1) I like them; 2) That would take years; 3) That would be excessively expensive 4) I like them.

Yes, realize that I am short but short (heh) of surgery there isn't too much I can do there.

Enhanced women comment: That is wild. Those brainworms are burrowed deep.

Yep, friends are too woke. That is the issue.

Update on date: Went and grabbed tea, no walk. Chatted for a few hours. She has a good sense of humor and great taste in music. Planning on a second date to go shopping for records/vinyl and grabbing brunch.

Glad to hear their date went well, OP. If you like this woman, try things differently this time. Spoil her rotten. Throw caution out the door. Don't wait too long to roll out the red carpet. You are already eccentric -- you might as well go all out. And kiss her on the second date. Don't wait.

[Anonymous]

Super glad to hear that the date went well, OP! Please don't leave things in limbo to set up the next date. Get it on the books today! Remove any question she may have about whether you are interested in getting to know more about her. That doesn't mean you're committed or certain she's the one. It just means she doesn't need to worry about whether you're interested. Ask a ton of questions about her and hold back from talking too much about yourself. Make it about her, not you. Plus, you need to delve into who she is as a person and assess her values sooner rather than later. Don't do anything expensive or over the top like sending expensive flowers. But maybe show up for date two with a book that you mentioned during date one. Or check out an article by someone she mentioned during date one. This shows her that you listened and that you devoted your time and energy to learning about something that matters to her.

[Anonymous]

Can we DROP this thread already. Enough of the pity party.

[Anonymous]

Anonymous wrote:Not trying to help a cause. Sorry that you don't expect a "real man" (whatever that means) to...express empathy? The question was asked whether I was trans and I answered in the negative with a chaser to make clear that I support a community that is going through a lot right now. That may not be a part of the world of the men you date but it's a part of mine so I'm going to speak on it if I feel like I need to.

I don't hide any aspects of my personality, whether they neatly fit into masculine or feminine or in between. Sometimes I wear pastels, sometimes I don't. Sometimes I'll binge watch romcoms on Netflix, sometimes I'll go spar with people at a boxing gym. Life is so much better when I don't confine myself to activities, or saying things that only "real men" say.

That being said, I have a first date lined up with a friend of one of the artists that did some of my tattoos. She's straight edge, so we're going to go grab some decaf beverages (she considers the caffeine a drug) and go for a walk, weather permitting. Seems like a nice person, with a solid career (owns small CPA firm focusing on tattooers/piercers/etc). She's seen pictures of me and has no issues with the tattoos since she is also heavily tattooed.

Ok well you are clearly clueless about what gay men do

[Anonymous]

I bet if you had never gotten tattooed so much you wouldn’t be on here asking this question.

[Anonymous]

Record shopping is super boring.

[Anonymous]

Reading between the lines with the Curtis Mayfield reference is that you are African American?

So forgive me if that is the wrong assumption. I’m a black woman who grew up in a predominantly white and Asian area. Are you attempting to date interracially? If so that could be part of the problem because just from my observation and if you look at statistics from OLD most non-black women prefer other races and just observationally my white/asian friends who have dated outside their race go for athletic, tall, conventionally attractive black dudes OR they’re women who are a little on the bigger side.

My DH is white so I don’t have direct knowledge but I suspect you may have better luck pursuing the type of women who put a high priority on “black love” as you have a lot to offer outside of looks.

[Anonymous]

OP, you are in the 15th percentile of men's height. You look like Curtis Mayfield, a balding guy with glasses. Those are major dating handicaps. You friends say "niche" because they don't have the heart to say "short and ugly". I'm brutally honest, but I got your back, bro.

Fortunately, many women don't care about looks if the man exhibits status and money. You are a financially stable law partner. But you are muscular with tattoos. That is tricky, because tattoos attract artistic, expressive women or women who like physical meatheads. There are many single professional black women in D.C., but you don't look like a law partner.

You could experiment with athletic/alternative leisure wardrobes. But in most contexts, you would do better with preppy Brooks Brothers and Ralph Lauren Polo outfits. You need outfits that convey your professional status.

Get shoes that add height (boots with heels, lug soles, padded running shoes or Nike Air Force One's). Going from 5'6" to 5'9" takes you from the 15th percentile to the 50th percentile, effectively tripling your dating market. If you date interracially, then you might succeed with shorter Asians and Latinas.

Professional women in Baltimore are more appreciative of educated professional men. While there are a lot of professional black women in D.C., there are also a lot of professional black men.

Finally, are you "weird" or socially uncalibrated? It is conceivable to accidentally go on two dates with different transwomen. I was just an annoying waste of time, so why are even mentionit here? You should not bring up silly, creepy, incriminating stuff on dates. Also, you must ruthlessly reject bad matches and time wasters. Online dates get a couple rounds of cocktails and a goodnight kiss. Second and third dates might get a little food because they last longer. Then it is time to visit your condo for a nightcap or Netlflix and chill. Any flaking, rudeness or lack of progress demotes the woman to back-up status.

I prefer online dating where the women see your photo. I think dating services are overpriced marketing scams. But "It's Just Lunch" could be timesaver if you are willing to spend a few hundred dollars to meet some women. More generally, you need to experiment, get good professional photos and good profiles on dating sites, try a bunch of different dating sites, try Speed Dating, try everything. Treat this like a part-time job. Get 1-4 new online dates per month, plus Speed Dating, or It's Just Lunch, and singles events. You will improve your dating skills with practice and stop chasing disinterested women and bad matches.

[Anonymous]

You lost meat 5’6” and BMX racing.

[Anonymous]

Anonymous wrote:You lost meat 5’6” and BMX racing.

Not meat- me at

[Anonymous]

I’ll be the one. Are you a giver? Do your partners love kissing you? Can you be emotionally intimate and tear things up in the bedroom?