Ok, here goes...

You only have so many hours in a day, days in week, and--not to be morbid--years left in your life. Fretting about the future will do you no good; I'm a professional fretter and I'm fully qualified to tell you it's a complete waste of time. Quality of life goes way up when you drop that stuff.

The better investment is to spend your time developing yourself: gym, hobbies, work, education, whatever matters to you, makes your little heart sing, makes you more you. (Sounds like you're doing at least some of that already.) Develop your skillset, whatever it is. Explore your interests. Learn. Accomplish goals. Because you love it, and it's good for you. You'll have fun, you'll grow, and you'll like yourself more.

Drop the concern about attracting a mate, and focus on making yourself more attractive to yourself. If you enjoy reading nerdy fantasy novels (for example), drop the trepidation "I'll never get a boyfriend that way"--and read the hell out of some nerdy fantasy novels. Some fine day, you'll be in the right place, at the right time, and find yourself in an opportune conversation, and you'll slay because of your experience, fund of knowledge, confidence, and passion. Confidence, mastery, and people enjoying themselves are universally attractive.

The insurance policy: even if you never find Mr. Right, you'll have spent your life enjoying yourself, doing stuff that matters to you.

That's Phase I. Phase II is forget about waiting for someone to approach you, and take the initiative--if and when you come across someone that intrigues you. You know you're ready for Phase II when (the thought of) rejection doesn't rock your boat or dampen your spirits.

TL;DR: Do you, and ask for what you want.

No one asks me out either, in fact I wasn't very popular in my twenties either. The moment I stopped looking for a date and just decided to"do me" and genuinely enjoy it, people suddenly got interested. Go figure. As some already suggested, choose an activity you have always wanted to try, meet people there just for the sake of company and watch it unravel. I asked my husband out on the first date by the way

Don't wait to be asked out, women can ask also. I f there is a nice guy and you know he is single, ask him out for coffee.

I agree with the person who suggested joining some sort of activity - an art class, a yoga class, a class at your gym? If people are engaged in the same activities you are interested in - there's more of a chance of compatibility. - And use a taxi service/lyft/whatever to meet someone safely and not on your turf should you progress to a meet up. Good luck! And know sometimes it takes time.

You're in Colorado Springs- one of the scariest places in the country. Saw an "Obama is a communist" billboard there. You don't want to meet someone in a bar probably... Dating alcoholics is not a good idea. So, when and if I go back into the dating pool, I'm going to consider volunteer work. Ok, volunteer work where I can't crank it out from my computer at home. Yeah talking to and meeting new people is going to suck. Democratic clubs, rescue animal clubs. You are an artist? There are probably artsy clubs to join nearby? Manitou Springs is pretty cool.. They have to have some art classes - maybe some you could even teach?

Go to events you like. Like my friends (going on 10 years) met at a shooting range. It took her 3 months to get up the courage to go alone and do what she loves, and then she met some one in the same head space. I met mine in the army but it was our love of writing and drawing that got us talking. Another of my friends were brought together by magic the gathering.

In the Denver area there is a thing for single people to go on adventures as groups, it's called "Events and Adventures". Try something like that, and good luck!

Perhaps you should do the asking. In today's world it's not a faux pas for the woman to be the instigator. Best of luck.

You might try asking a man you’re interested in out instead of waiting to be asked.

Preachin' to the choir. Been single for 2 years, but I've given up looking.

I've been single for twice as long.

The reason is nobody is prepared to handle how awesome you are. They don't want to be shown up.

Break the mold some; if you find someone attractive you should ask them out.

Its been my experience that when you hunt a relationship you won't find it.havent you ever notice that nobody wants a man till somebody else already has him? I suspect its the same for you if your single people wonder why and they shy away.as soon as you get a boyfriend you will have suitors climbing out of the walls. human beings are really good and being dense

Idk, maybe you do the asking? May be something you’re projecting, strength, intimidation, who knows? May be random events, too.

I think it is the locale.

I wish I knew, then I'd have the answer to my own dating scene.

I absolutely do agree with everyone that has said, "lose the headphones", they're right, they make you unapproachable.
Come up to Denver, I live right by the Bluebird, Ogden, & Fillmore theatres, I'll take you to a concert (I think you're beautiful and can't personally see why anyone wouldn't want to ask you out). The Springs is not the coolest place, you should be hanging in Denver where the people are much more friendly and liberal and the music scene kicks ass.

I actually have a good article about your predicament. Most men will not approach you. Or any woman. There is a certain percentage who approach most women they are attracted to...but most will not for various reasons. I'm looking for the article. I'd be interested in what others think of this and why they don't approach women that interest them....

There are some good comments and advice on your post but I also remember some things you've previously said on this site. You have had some extremely bad things happen to you including intimate, physical betrayal. Are you sure you're ready? If not you may be putting off a vibe that is not welcoming. Definitely not saying that something is wrong with you but maybe there's some more stuff to work through? I've said this to a lot of folks but there might be some groups for non-believers/skeptics on Meetup you could try. It does sound like you're getting good at reading people enough to figure out who to avoid. I think you've said you're seeing a therapist? What do they say? Take care.

Do you like to dance at live shows? If so, here is my advice... Get yourself an Audio book version of that old classic, How to Win Friends and Influence People. Listen to it on your headphones, study it some. Then on your nights off, go to some really groov'n live rock shows, get totally absorbed in the music (without those headphones), forget about anyone else there and just dance your ass off for you! Between songs ask the person who has been dancing up next to you if he/she wants to talk. Which they will. Employ a little of the basic principles from 'how to win friends and influence people', and you will get dates if you want them. Just make sure you take Uber home. Never leave a night club with a guy you just met.
I also do think that organization "It's Just Lunch" might work well for you. If you have the $$$. Either way, I'd probably skip the library for the homeless.

Because the world is a horribly unfair place, and only through scrabbling in the muck can we possibly find our diamonds in the rough!

Sarah If I lived in Colorado, I would ask you out in a minute. I love intelligent women. For me it is a great turn on. My main problem is that I don't travel in the same circles as they do, and I am still a little shy. I didn't have a lot of confidence with women when I was younger, and now that I am older and wiser, it seems they don't want me because I am not a rich, young handsome stud, and as the song says "melt a young girls heart with his pout". I am not saying I want a young girl, but most of the women my age and a little younger in my area at least spend a lot of their time worshiping a fairy tail or chasing after their youth with some boy toy, or they are chasing the golden ticket to a life of ease. Keep searching, you will find someone to love. I am always here for you, my friend.

Unfortunately, you happen to live too far from me and we are, as they say, geographically undesirable and inconvenient.

I absolutely do agree with everyone that has said, "lose the headphones", they're right, they make you unapproachable.
Come up to Denver, I live right by the Bluebird, Ogden, & Fillmore theatres, I'll take you to a concert (I think you're beautiful and can't personally see why anyone wouldn't want to ask you out). The Springs is not the coolest place, you should be hanging in Denver where the people are much more friendly and liberal and the music scene kicks ass.

For one and obvious reason thusly you have a complaining and dwelling issue. It is what it is.

Being intellectual also has a tendency to make us colder when we probably should not be. If you are overly facts before feels you may go through the cycle I go through when I like someone and completely lose your fucking marbles because your feels are still in there infancy and when they take control oy vey all bets are off. That tends to creep people out.

Then there is the whole your ideology, are you a SJW if so that equals I am not playing with the possibility of being falsely accused of rape and that is also part of it now even if you are not a SJW people have far more fear towards women due to them for all we know the next woman we end up with will become the new mattress girl society favors women over men. Then there is the are you vegan bit where vegans swear they never speak of their vegan ways but it is like running into a bloody religious person trying to convert you to veganism.

Personality, ideology, and brains play a key role plus looks. A person like me prefers smarts but if you are hideous I will notice partially due to me being an artist I pay attention to details way more than others I notice things I shouldn't sometimes good sometimes bad.