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

[Anonymous]

You are very short for a man. You should only focus on women shorter than you.

Your height is not an issue for me but the tattoos are an absolute dealbreaker.

[Anonymous]

Get your tats lasered off.

Problem solved!

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

How are LGBTQ people part of the world of people you date?

Could have worded that better. I was trying to say that LGBTQ+ community may not be a part of the world that the men that the PP date, but said community is part of my world or "my universe" if you will. That is to say, I have friends and family that are part of the community, specifically some of the folks that I'm friendly with at my gym or that come to ride BMX with me and others at times. I have also dated a few transwomen, but once we got to the stage where I was made aware they had transitioned, I politely broke off any romantic pursuits. Still chat/hang out from time to time platonically.

Ah. There’s the buried lede.

To say the least!

OP, if you had led off that you're a tattoo-covered man who has sex with biological males and doesn't want kids, this thread would have been very short. The fact that you're playing out this whole farce here and doling out crucial info only when people ask the exact right questions also tells me that you're sneaky and secretive. I'm sure there's more you haven't shared here. You already know why you don't appeal to women and why the few who stick with you run for the hills as soon as you start to show your real self.

DP.

Do you see "trans" on a page and your brain switches off after that? Go back and read what you think you are responding to from OP?

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

How are LGBTQ people part of the world of people you date?

Could have worded that better. I was trying to say that LGBTQ+ community may not be a part of the world that the men that the PP date, but said community is part of my world or "my universe" if you will. That is to say, I have friends and family that are part of the community, specifically some of the folks that I'm friendly with at my gym or that come to ride BMX with me and others at times. I have also dated a few transwomen, but once we got to the stage where I was made aware they had transitioned, I politely broke off any romantic pursuits. Still chat/hang out from time to time platonically.

Ah. There’s the buried lede.

To say the least!

OP, if you had led off that you're a tattoo-covered man who has sex with biological males and doesn't want kids, this thread would have been very short. The fact that you're playing out this whole farce here and doling out crucial info only when people ask the exact right questions also tells me that you're sneaky and secretive. I'm sure there's more you haven't shared here. You already know why you don't appeal to women and why the few who stick with you run for the hills as soon as you start to show your real self.

DP.

Do you see "trans" on a page and your brain switches off after that? Go back and read what you think you are responding to from OP?

DP. No straight man finds himself dating multiple transwomen. He’s somewhere on the queer spectrum and not being upfront about it. We could have gotten to the answer on why he keeps striking out 16 pages ago if he had led with that.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

How are LGBTQ people part of the world of people you date?

Could have worded that better. I was trying to say that LGBTQ+ community may not be a part of the world that the men that the PP date, but said community is part of my world or "my universe" if you will. That is to say, I have friends and family that are part of the community, specifically some of the folks that I'm friendly with at my gym or that come to ride BMX with me and others at times. I have also dated a few transwomen, but once we got to the stage where I was made aware they had transitioned, I politely broke off any romantic pursuits. Still chat/hang out from time to time platonically.

Ah. There’s the buried lede.

To say the least!

OP, if you had led off that you're a tattoo-covered man who has sex with biological males and doesn't want kids, this thread would have been very short. The fact that you're playing out this whole farce here and doling out crucial info only when people ask the exact right questions also tells me that you're sneaky and secretive. I'm sure there's more you haven't shared here. You already know why you don't appeal to women and why the few who stick with you run for the hills as soon as you start to show your real self.

DP.

Do you see "trans" on a page and your brain switches off after that? Go back and read what you think you are responding to from OP?

DP. No straight man finds himself dating multiple transwomen. He’s somewhere on the queer spectrum and not being upfront about it. We could have gotten to the answer on why he keeps striking out 16 pages ago if he had led with that.

Not necessarily. He has eccentric looks, and that may be more attractive to certain people. This does not necessarily mean these are the people he would like to attract. Hence he is here, asking for advice.

[Anonymous]

Anonymous wrote:Have been trying to date over the past few years and after a very very large number of rejections I bit the bullet and asked a couple of my friends what they thought was going on. To my surprise, all of the women said that I have "niche looks" meaning they thought that while I'm not "ugly", I'm not traditionally attractive for a guy. They don't think I'm the equivalent of Steve Buscemi or anything along those lines, but I'm no George Clooney or Patrick Dempsey either. This kind of makes sense because of my dating history in that over the past few years I've dated dozens of women with varying amounts of success. Some only wanted the first date, some lasted for 6 months, but that is the extent of it.

To provide a bit more context, I'm 5ft6in tall, very muscular and fit. My celebrity lookalike is Curtis Mayfield, but I cannot sing like him unfortunately . I own a condo in DC and I work as a partner at a boutique law firm in a finance practice. I have a fair amount of hobbies (obviously weightlifting/exercising, BMX bike riding, collecting tattoos, perfecting my beef wellington) and a solid friend list, and I have never heard from anyone that I'm "boring" but I'm not putting it past there being some sort of social defect as well that is preventing me from making a solid connection with someone. I provide that info not to brag or point out that I'm a catch but to establish that I have my life in order as a baseline. The women that I have dated have never brought up my "niche looks" but usually would tell me they just weren't feeling it and I did not want to pry or try to force them to come up with a "reason" for not wanting to continue to see me.

Do folks have any thoughts here, absent plastic surgery, that I could use to improve my dating life in this regard? Do I need a matchmaker? The vast majority of women that I've dated have come from online dating as I'm not one to approach in person IRL other than two one-offs over the years.

I didn't read the thread. I went on a date with a lawyer in a finance practice once and he was so dull. That said, He probably didn't ride BMX or collect tattoos. Maybe your forever is on another continent? Start traveling.

[Anonymous]

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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

How are LGBTQ people part of the world of people you date?

Could have worded that better. I was trying to say that LGBTQ+ community may not be a part of the world that the men that the PP date, but said community is part of my world or "my universe" if you will. That is to say, I have friends and family that are part of the community, specifically some of the folks that I'm friendly with at my gym or that come to ride BMX with me and others at times. I have also dated a few transwomen, but once we got to the stage where I was made aware they had transitioned, I politely broke off any romantic pursuits. Still chat/hang out from time to time platonically.

Ah. There’s the buried lede.

To say the least!

OP, if you had led off that you're a tattoo-covered man who has sex with biological males and doesn't want kids, this thread would have been very short. The fact that you're playing out this whole farce here and doling out crucial info only when people ask the exact right questions also tells me that you're sneaky and secretive. I'm sure there's more you haven't shared here. You already know why you don't appeal to women and why the few who stick with you run for the hills as soon as you start to show your real self.

DP.

Do you see "trans" on a page and your brain switches off after that? Go back and read what you think you are responding to from OP?

DP. No straight man finds himself dating multiple transwomen. He’s somewhere on the queer spectrum and not being upfront about it. We could have gotten to the answer on why he keeps striking out 16 pages ago if he had led with that.

INDEED, INDEED

Turns out the OP was not being honest.

Also, turns out imho that this thread would not have been nearly as long if the respondents were not so intent on supporting the OP. I think this may be a case of Black privilege. If a short white man covered in tattoos that was on the queer spectrum, was the OP, then the support would be vastly different. Nothing wrong with being queer as an adult, but honesty is important when seeking advice. Although, I'm partly guilty of that also. I as well had wished to give him positive feedback, partly because he's a POC. I'm not saying it's right or wrong, just that it was an influence as to why this thread is 16 pages on a person that is so "niche" that it's hard to give him solid advice of the things he can change. Am I wrong !

[Anonymous]

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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

How are LGBTQ people part of the world of people you date?

Could have worded that better. I was trying to say that LGBTQ+ community may not be a part of the world that the men that the PP date, but said community is part of my world or "my universe" if you will. That is to say, I have friends and family that are part of the community, specifically some of the folks that I'm friendly with at my gym or that come to ride BMX with me and others at times. I have also dated a few transwomen, but once we got to the stage where I was made aware they had transitioned, I politely broke off any romantic pursuits. Still chat/hang out from time to time platonically.

Ah. There’s the buried lede.

To say the least!

OP, if you had led off that you're a tattoo-covered man who has sex with biological males and doesn't want kids, this thread would have been very short. The fact that you're playing out this whole farce here and doling out crucial info only when people ask the exact right questions also tells me that you're sneaky and secretive. I'm sure there's more you haven't shared here. You already know why you don't appeal to women and why the few who stick with you run for the hills as soon as you start to show your real self.

DP.

Do you see "trans" on a page and your brain switches off after that? Go back and read what you think you are responding to from OP?

I said what I said. Bye!

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

How are LGBTQ people part of the world of people you date?

Could have worded that better. I was trying to say that LGBTQ+ community may not be a part of the world that the men that the PP date, but said community is part of my world or "my universe" if you will. That is to say, I have friends and family that are part of the community, specifically some of the folks that I'm friendly with at my gym or that come to ride BMX with me and others at times. I have also dated a few transwomen, but once we got to the stage where I was made aware they had transitioned, I politely broke off any romantic pursuits. Still chat/hang out from time to time platonically.

Ah. There’s the buried lede.

To say the least!

OP, if you had led off that you're a tattoo-covered man who has sex with biological males and doesn't want kids, this thread would have been very short. The fact that you're playing out this whole farce here and doling out crucial info only when people ask the exact right questions also tells me that you're sneaky and secretive. I'm sure there's more you haven't shared here. You already know why you don't appeal to women and why the few who stick with you run for the hills as soon as you start to show your real self.

DP.

Do you see "trans" on a page and your brain switches off after that? Go back and read what you think you are responding to from OP?

DP. No straight man finds himself dating multiple transwomen. He’s somewhere on the queer spectrum and not being upfront about it. We could have gotten to the answer on why he keeps striking out 16 pages ago if he had led with that.

In addition to dating multiple trans women, OP has also dated multiple women on steroids. I wonder if any of the women OP has dated were born female.

[Anonymous]

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]

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.

[Anonymous]

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.

[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.

If you say so. OP can date whoever he wants, but like PPs have said, this part of OP's dating history is pretty crucial. I think OP knows this.