Not a dude but I'll answer anyway because heteronormativity is for chumps.

My biggest challenges are that I'm shy and socially inept, and that it seems like all the lesbians in Tacoma are hiding and/or already in relationships. Unless, of course, they're lying about being taken to get me to go away....

My biggest challenge when it comes to meeting and connecting with women is my wife.

That was tongue-in-cheek. I've been married to a wonderful woman for a long time now and would not consider changing that.

Well. First off I will only consider non religious women. The available list is small because fewer people are not infected with religion.
Second , it seems like non religious women are skeptical and harder to get to open up to you. Seems like they are hesitant to meet with you.
Then there is the whole metoo thing. We are afraid to suggest even meeting for fear we will be accused of something.

Now you. Same question.

Let me add.
I am looking for an intelligent woman who is also personable. I tend to trust people , probably too much, and I am looking for someone who trusts a me. She will not be disappointed. I am trustworthy and willing to prove it but only to a deserving person. Treat me like shit and I will give you nothing. Treat me well and like you wish to be treated and you have 110% percent of me.
I am also a passionate person. Looking for the same in a woman. Don't expect me to " never offend you" because I will speak my mind when I feel comfortable around you. I mean no offense, I am just being honest and in some cases do it just for fun. Besides, your reaction is not my responsibility. It belongs to you and you alone.
I am.tired of people who are so easily offended and so quick to judge and categorise you. I am a person, me. Please don't associate me with someone from the past. I am not them. I am me.
So many times I have heard
" he said the same thing and ___
What you guys all want is ____
He did the same and ____"
No. I am not anyone else. I am me. If you want to know what I meant or what I think or how I feel, just ask. I will tell you the truth. Every time.

What I am looking for is probably the same thing you are.looking for and the same thing guys are looking for...
Honesty, passion, trust, opened , acceptance.
Seems hard to find these days

Finding and meeting smart women who have taken care of their minds and bodies into their 50's & 60's is a huge challenge within a rural area like West Virginia. Few people, terrible choices. While I don't mind a long drive, it places enormous pressure on a 1st-meet. I love 95% of the lifestyle here, but there simply is NO quality social life available for an educated guy who expects more.

Female instead of male, but I think our issues are similar. Most of the people my age (49) are either married, divorced and bitter, or in a relationship. When I do meet interesting people, I think I tend to scare them. I’m very direct and can be “intense.” I don’t do the coy, shy, pretend-you-aren’t-interested crap that some women do. I also don’t have children and strongly prefer not to date anyone whose kids still live at home.

Religion tops the list for me. Other than that, possibly distance

I can make friends all day, but when it comes to flirting or picking up on hints or vibes for anything more I'm clueless. I've had friends tell me someone was obviously flirting with me and wondering why I didn't say or do anything; to which I can only respond I had no idea. Once I know someone is interested for sure I can usually handle myself, but it's the trying to figure it out and show I am interested that I struggle with.

I think if I knew then I'd already have a girl by my side and be happier. I don't go out a lot but I do meet girls but seem never to find one that loves me as much as I love her. I have a lot of girl friends who all seem to agree that I'm a really nice guy and previous girlfriends have seemed shocked that I'm single, when they get to know me. But finding a girl who sees me as a boyfriend and not just a friend seems to be really difficult.

Where I live.

Meeting them in the first place! I don't drink, so the bar scene is no good. My job doesn't involve any conversation more in-depth than 'your total is...', so it's not helpful. And I don't (often can't) get out much for other social activities. Somehow I doubt the 'perfect woman' is gonna just knock on my door... ?

There is a combination of intelligence and sensuality too few women allowed to come out at a first meeting.

Trying not to undress them with my imagination

I'm no longer in the market, but my biggest challenge was actually meeting someone I had something in common with. Most of the women I met would start getting on my nerves 30 minutes after I started talking to her. The ones I liked were usually in a relationship.

Generally I seem to scare people.
It's not just me, many people have told me this.
Look, mannerism, the way I speak and what I speak of....a lot plays into it including their issues. It's something I've lived with most of my life, but I do know it prevents people, not just women, from interacting.
I'm the kind of person most people "keep an eye on".
Someone got me a T-shirt that says Trigger Warning on it.
?

I think I tend to be too concerned about other people's personal spaces. And I think this feeling is ampliphied when I try to reach out and connect with a woman.

It's not a confidence thing, because I feel like I have a bunch of decent qualities, I just get a feeling like I don't want to barge in on someone's personal space.

I'm 46 and single women are either too young or too old. I'm also pretty happy being single so I don't put much effort into dating. I figure the right one will come along eventually.

Finding women with similar interests. Aside from that my instincts take over, and the rest is really not that difficult.

I would love to know, who came up with this male model that most men do.
Men have to ask the woman
Men have to pay for the entire time.
It's not easy for guys. I'm 57 a widower and I still don't find meeting women easy.

I've resorted to chemistry and realizing it is there. Once the chemistry seems to be mutual I explore it.

Honestly?

Just meeting people at all is a challenge.

I’m a train driver so work shifts. And when I do have time off work I have my son.

On the very rare occasions I’m kid free and get out and about, well I think I’m a bit too odd. An old school goth, sci fi fanatic ages over 40? I’m fact closer to 50 now.

I think it safe to say I’m in a bit of a niche.

I'm actually good at meeting women. I work in sales so I meet plenty of people that need my help. Unfortunately most of the women here are good Christian or Baptist women. But when your warm, nice, funny, laid back, employed, and a good kisser religion doesn't come up right away. There are plenty of other topics to steer too.

As a male, if you don’t actively try to ‘get’ with women, then you aren’t going to connect. I would say that’s my biggest challenge.

To be honest, it is the feeling of inadequency. Though I tend to have a lower self esteem then most. A girl can flirt with me and I can over think it to where she wasn't flirting. I feel I have a big heart but socialital wise I don't fit the mold I'm expected to.

Well, there is the problem of where... The bar scene is not the place to find real connection and most social events I attend are not really full of singles. And dating apps have been pretty unlucky for me.
Also, I have a problem with anxiety. I am usually afraid to approach without some liquid courage, so I find women in the wrong places. (Also, afraid is kind of a poor term--I convince myself that there is no mutual interest, even when there seems to be, or that there would not be, because she is out of my league.)
Then there is the problem of being forward enough without it being too much. I have a lot of trouble with this one, especially because a notable percentage of women think I am gay when they first meet me.
Finally, there is my weird issue with touch. I did not even touch my girlfriend's hand on the first date or half the second date. I never have a good feel for whether it would be wanted. (I am also the guy who asks permission for the first kiss goodnight, which I know is a turn-off for some.)
But, hey, despite all that, it sometimes works out.

Opportunity to meet then having real chemistry