I’m not gay (married with two kids). No apology necessary though.
By they way, aren’t you the marathon runner who never goes to the gym? Or am I thinking of someone else? 
I got all of that down except how do you go from “nice smalltalk” to “I am interested in you” without scaring them off?
But I’m hardly the only one like this. Believe me, there are people far more extreme than I am. They have no trouble finding interested women.
Have a way to feed their babies.
If they were looking for marriage material, yes, that’d be a huge concern. But in college? When everyone is in debt and poor, even the comparatively well-off weed trimmers?
When I have two hundred peers in the same program who are equally poor and destined to be almost as poor and who are still having no such trouble finding sexual partners, clearly I am doing something wrong that has nothing to do with my choice of industry.
True enough, I guess. Unfortunately, the creep factor is very hard to judge over the internet. Maybe go to a dopefest sometime and we can see what’s what.
You guys have given Reply some good advice. I’m tempted to start a female version of “30, never had a relationship” thread. You know, just to see if it’s the same advice.
I goddamn guffawed at this.
Randy, hush.
Okay, we gotta work on the “desperate clown” thing. Not a good look. Women can smell desperation from a mile away, and it smells like the inside of a Taco Bell. Gotta work on walking the tightrope of seeming interested but not desperate. Let’s work on this. Also, building confidence I’d reckon is more important than getting fitter. You’re not in bad enough shape that it’s an automatic disqualifier for most women. What will dry women up in a New York nanosecond is lacking confidence. It’s probably the most unattractive thing a man can do.
So how, you may ask, does one build confidence? Hell if I know. Maybe someone smarter can help you out with that. I’m a fairly confident person, but I have no idea where it comes from. I’m not particularly beautiful or brilliant or rich, but I still really like myself. I guess a lot of it comes from not giving a fuck what other people think. They’re just as dumb and clueless as I am, except I’m way more fun to be around.
And for the record, I was only half kidding about the 18 movie thing, but I was also 100% completely serious. In general I’m annoyed when someone’s asked to name a favorite anything, and gives me a 20 item list.
Edit:
It is. Get confident, fit, and friendly.
Paralyzed gym rat; but you were close. 
Done, done and done. OK, thanks.
It shouldn’t be a huge jump! It’s not going from “hi, we’ve got something in common” to 2 minutes later “would you like to marry me?”. Conversations develop along the lines of “hi, we’ve got something in common” … general chit-chat … “would you like to catch up and discuss (what we’ve got in common) another day?”
You mentioned up thread that you sat and talked to a girl for hours - so in all that time there must have been plenty of opportunities for you to (if you wanted to) mention a nice coffee place, restaurant, park, movie (insert anything you had in common) that you could do with the other person at a later date … and as the conversation rolls along you could have asked for phone/email details so you could stay in contact.
Perhaps practice setting up conversations so that you don’t have to ask them on a DATE at the end … leave hints along the way. Asking for their contact details could be done before the end (if you know a great website that would be a shared interest, ask for her email, take it down, keep talking) … the less emphasis you put on the ask, the less you’re going to sound weird about it and make them worried about giving out contact details.
A point that relates further back into the thread … you said that you wouldn’t have anything in common with someone who worked for certain types of companies … sometimes people do jobs that they don’t actually believe in because they need the money and sometimes people will change. I’ve worked for some of the worst environmental companies in the world and now I work in the charity sector.
OK. I’ll try that.
Just a note though: In the past I’ve done similar things and we usually ended up becoming friends. I’m pretty sure they see me as the nice, harmless, potentially gay friend, not the man they’d want to be with. Any way around that?
Flirt.
Heh, I suppose I should point out – in case it wasn’t obvious by now – I don’t really know what that means.
How does one… “flirt”?
Explain it to me like I were Data from Star Trek, utterly unfamiliar with human mating customs.
This is it. OP, sit down and figure what you’re proud of and why you do what you do, and fuck what anyone else thinks. Just focus on doing things you like without wondering how it might or might not lead to a relationship. It’ll come, and here’s the rub: It’ll come when you’ve finally, FINALLY truly decided you really don’t need a relationship after all. Then she’ll bounce in and pretty much fuck up all your plans. But at least she’ll let you touch her for a while.
It can be hard. That’s why I would tend toward recommending online dating when people are first getting started in real dating, just so the participants up front expect “date” behavior, not “friend” behavior.
But, in general, you have to flirt.
And I see I was ninja’d by Ambivalid.
ETA: Ninja’d by everyone!
A well-timed nipple tweak can work wonders. When it doesn’t land you in the slammer.
Smiling, lots of eye contact, use of humor that infuses recognition/appreciation of the girl’s beauty and/or brains, a bit of self-deprecation and an underlying confidence beneath it all (even it it’s faked at first).
Self-deprecation is very hard to get right if you’re inexperienced or not particularly confident. Use it much more sparingly than you think you should.
Flirting would be hard to explain to Data because it’s all about reading signals and responding appropriately, but here goes.
Look toward her face, especially her mouth, when she’s talking. Not intensely focused. People’s eyes tend to travel around. Let that happen. Look her in the eyes on occasion, but DO NOT STARE INTO HER EYES. It’s incredibly intimidating. Make eye contact, then let your gaze go elsewhere. If she meets your eyes and holds it, that’s good. If her eyes skitter off, that’s bad.
Depending on the seating arrangement, try to sit where you’re relatively close, but not immediately touching. Give her some space. Do not crowd. If you’re side by side, it’s okay to bump shoulders or arms, but you shouldn’t be glued to her. If you do touch, smile at her.
If you’re sitting across from one another, change your position on occasion, lean a little forward when she’s talking, a little back when you are.
Sit in a relaxed but not sloppy way. Not tense, but not lounging. You want to make it clear you think she’s interesting, but you do not want to be scary intense. If she starts touching her hair or her face, that’s usually a good sign. This isn’t true if she starts nervously biting her nails or something!
If you want to ask her for her number and you’ve been talking for a while, touch her when you ask. Very briefly, not grabbing. Just touch her hand or forearm and say something like, “I’ve enjoyed talking with you and would love to continue sometime. Can I see you again?”
These are kind of basics, and like everything they can be done badly.
NO STARING! I can’t say that enough. 