It’s not that it’s not good enough, it’s that it’s just plain not enough. It’s not like you can build a relationship out of discussing how fit you are and going clothes shopping. Presentability will get you at most the first 5 minutes of one date. After that, your potential paramour is sitting there thinking “Okay, what else you got?”
If you don’t have humor or charm or humor or shared interests or similar values to offer at that point, you’re toast, and rightly so.
Unfortunately, I’m not even making it to the date or even the conversation stage. I’m being shot down when I ask to dance with a girl at a bar, or I buy her a drink or whatever. 100% failure rate. The only women I made it to the conversation stage with are the women who pursue me first.
There’s something about my appearance that’s not sparking attraction with many women. Men, on the other hand, I have more luck. That’s the part I’m clueless about. I feel there’s nothing wrong w/ me. I’m normal height, fit, well-endowed, I dress well. I smile. I spend a lot of time and money on my hair. I guess I do have a strike against me, I’m kind of guyish…but some women are into that. I’m not led to believe that I’m being turned down by that many women because that reason.
As for my interests and personality…I think I live a varied life. I’m into outoorsy stuff, travel, dining, gambling. I have some geeky interests such a video games and role-playing (but not LARPing :p). I got a lot of friends and have an active social life. They would describe me as funny and quirky…actually the opposite of my buttoned-down appearance. Honestly, I would rock the tattoo and piercing look, but I’m not a musician or otherwise strongly artistic, I don’t want to be a poser.
My point is that I’m very frustrated that despite the time and money I put into my appearance, I put MORE effort into appearing non-threatning - hence the button down look. I’m getting nothing in return. I always hear women, regardless of orientation, complain about how frumpy some people look. But at the end of the day I don’t think it matters to them.
And, speaking of friends, it is mystery to them why women react to me the way they do, also. Apparently, one friend and her sister had a long discussion about this and could not come up with anything (I wasn’t present, my friend just told me about the convo), other than trying to meet women at different venues.
So you don’t like being left or passed over for people who seem richer/more stylish/hotter than you, and you don’t like being left or passed over for people who seem uglier/less chic/less cool than you. Nobody does. When you’ve been dumped for someone else, or are going through a dry spell, it’s just as easy to complain that men or women are shallow and only go for hot sluts… or that they’re stupid and blind and ‘Hey, I’m WAY hotter than her!’
Yours is an eternal question. On the bright side, you seem pretty self-aware, and like you might actually listen to a friend’s advice if they could figure out your hidden flaw. It could just be a numbers game. Despite what porn would have us believe, lesbians, actual lesbians who want relationships with other women, are a fraction of the population. Finding someone you click with is going to be a challenge based on that alone. Also, if you feel like your buttoned down look is to make yourself seem more approachable, don’t forget that some people want a little danger! It’s not like all bull dykes are begging for dates.
Nobody is answering the OP’s question. The behavior you are seeing is an example of how some (many?) women like to see a combination of strength and weakness in their partners. If you’d come across as the “underdog”, it would make you more relatable to those women. If that’s just not you, then it’s worth looking in different types of social groups (like maybe the sports or politics crowd)
Nothing much to add, except that we would be happy to have you back if you decide to return to the fold.
Perhaps these women are out there right now wondering what’s the matter with you that you’d rather chase after women who aren’t interested.
Wow! A chick that LARPS! I mean, wow! I think I’ve heard of that! Oooooh, kinky!
Uh… (Googles: LARP)
Hmph. Never mind.
What sort of LARP are we talking about, Vampire the Masquerade or D&D?
Gay or straight it’s that way for everyone.
I always get, “Mark I can’t understand why you can’t get a date.” I say, “Would you date me?” The answer comes back “Oh goodness no.”
But one thing I have learned in 46 years on Earth, if something happens to you more than once or twice, it’s you 
Eh? You don’t want to be a poser, so you dress like somebody you’re not? Is this some kind of whoosh?
And what kind of Billy Badass do you think you are that you put all this energy into “appearing non-threatening”? It’s not like quirky, funny people (with or without tats or piercings) are exactly scary.
I think you are likely still thinking like a straight woman. You’re concentrating too much on your appearance–not in the sense of dressing too nice, but in the sense of trying to look unthreatening. That’s a thing women have to do to get guys to hit on them. It’s not something you have to do to hit on others.
What I think you need to focus on is showing at a glance what makes you interesting or different. I’m not saying change who you are, but be a little more open with it. Your description of looking immaculate would make me think you were, well, boring.
But, really, the big thing is it sounds like you are trying way too hard. Why don’t you try not doing any of those things you are doing, and just going out. It won’t hurt if it doesn’t work, but it might ironically accomplish what you were trying to accomplish in the first place–appearing non-threatening.
(No, that’s not a contradiction. I’m saying don’t try so hard to look non-threatening.)
Whatever you do, don’t join a hiking ‘Meet Up’ group.
-d&r-
There’s no mystery to this. Men are sluts.* The view is different from the other side.
Look, I’m sure there are nuances of lesbian dating that I’m not privy to, but I think the heart of the matter is the same across orientations. Stop trying so hard. Get out and meet people and grow some friendships without sizing everybody up as a potential romantic partner right from the get-go. Let your real personality show instead of your auditioning-for-a-date personality. The more people you meet, the more chance a spark will occur somewhere with somebody, probably when you least expect it – it’s not something you can explain or control, so relax.
Dating is hard, but it’s harder when you obsess over how hard it is. Go with the flow and good luck to you.
*Yes, a gross generalization, but true more often than not.
This may be different in your scene, but, in every lesbian scene I have ever been privy to, picking up people in bars accounts for a tiny little percentage of the dating/hooking up that goes on. Lesbians date their friends, their friends’ friends, and their exes’ exes. Even people who hooked up in bars were usually within a degree or two of each other, socially.
Do you have lesbian and gay friends? Throw a pot luck or some sort of smallish party and have a few folks that know you invite a friend or two. Even if no one is your type/interesting to you/interested in you, you’d be expanding your social circle. And that’s how you wind up dating a lesbian.
Ok, as a guy - sorry, not a lesbian - don’t dress to look amazing, dress the way you like to look. For me what works is to feel comfortable with how I look but no more - overdressing just makes me feel like I’ve got something to prove, with makes me nervous and it shows. Besides, none of the recent dates I’ve set up seemed to mind me walking around in jeans and a t-shirt.
At the risk of analyzing my own problems: don’t ask people out because they’re “that perfect girl”, ask them because it would be a fun and interesting couple of hours. In my experience, that really does work.
::Lightbulb moment:: YES! it’s this. Generally speaking, I’m not sure most lesbians respond that well to being approached cold by a stranger in a bar. Attraction takes a little longer than that, even if it’s just making smoky eyes across a room to establish mutual attraction for a while before you talk. Being jogged at the elbow by some random at the bar asking me if I want a drink is always going to provoke a rejection. If I look at my relationship history, then pretty much everyone has been connected to me somehow socially, so the attraction has chance to smoulder away before any approaches are made.
The only one of my lesbian friends I can think of who is involved in a serious relationship with someone who just chatted her up in a bar was approached by a seriously hot confident Brazilian woman, and who’s going to say no to THAT?!
Oh, and on a purely superficial level, I’m not sure that ‘clean-cut button-down’ reaks sexy, necessarily. Worry about what the parents are going to think of you AFTER you’ve started the relationship.