I'm a man who's taught psych of relationships for 21 years and mostly heard about the trials of young men who couldn't figure out how to get a woman to be interested. So I'm feeling your shy-self-torture and thinking, "Wait a minute, it shouldn't be that hard. He already knows how awkward you feel around him, even if he's not sure of what to call it. But he knows you're interested in him."
What's he going to do about it when you finally get around to popping the question, or spend two more weeks trying to get him to make an unmistakable move? He's going to think/say "She's cute, she could be interesting. It's fun to flirt around, and it's worth some time to see what could develop--I like the mystery, since I don't know anything about her."
OR "I can't afford ANY more feelings/involvements now. My life's too complicated and stretched thin as it is. I don't want to hurt her feelings, cuz it takes guts to stick yer neck out like she has done. So I have to just not act very interested, so she'll get the hint to back off without thinking she's done something wrong. It's pretty flattering that a complete stranger would want to get to know me that much."
OR "Oh no. Now I'm going to crush this young spirit if I don't handle this right. I should have already made it obvious that I'm already involved, so she doesn't get really hurt and think I'm a slimeball for leading her on."
OR--well the other possibilities are in the less than 2% ingredients list at the bottom of the label, like I'm gay, I'm a serial killer, I'm an undercover CIA agent, I'm a professional con man, I'm an alien hiding out from the intergalactic police in a human body, etc.
Notice that thinking you're a silly fool would not show up in his thoughts at all, and he's just as concerned about doing the wrong thing as you are. That comes with the difficulty of first approaches for both sexes. If you can face all 3 of the likeliest responses from him, then there's not as much to worry about when the conclusion of this phase actually arrives. It's mainly in the waiting period before one of those outcomes that your awkwardness, worry and self-doubt can go higher and higher until it's too uncomfortable
to stand. So why not shorten that waiting period?
You're in a situation in which American cultural rules don't cover how to approach well enough, except to practice "plausible deniability," which means 'you do your best to test the other person's readiness to proceed to the nitty gritty of auditioning each other for a possible romantic relationship, but WITHOUT tipping him off that you're really interested, so that he could still think it's just accidental and you're just being friendly like you always are with most anybody. You try to get him to show you his "interest" card without showing him yours first,' But plausibly deniably flirting always risks the target person misunderstanding the gestures and assuming you are just being friendly the way Americans are supposed to be with everybody, so he won't risk showing you anything that's not plausibly deniable romantic interest either. And you're both stuck in a holding pattern while the intrigue and the awkwardness build up in equal amounts.
But women have another tool in their arsenal that is much less awkward, and that's "Proceptivity." That means she gives some signals that she'd be interested in talking with him if he wanted to knock on her door, or like waving the green flag at the racetrack so he's invited to rev up his engine and make a rush for her whenever he's ready. She's using her body language, her words, her rapt attention, etc to signal "I'm ready for a test drive whenever you are." Then she just waits, because her answer will come soon enough, unless he's too inexperienced or stressed out to notice..
We already know how to do that thru the dating sites and facebook etc. There's way less awkwardness & shyness because nobody can see you when you put up your notice. So why not do the equivalent in apartment complex ? Put a note on his door: "You seem like an interesting person, somebody that could be a good friend. Can we meet for a walk in the park, an icecream, coffee, or your coounterproposal. You can respond to my email: email@example.com (but a real email , not a joke).
That should get you over this what-if-I-blow-it self-torture phase a lot quicker. What do you think? Shirley, you're welcome to disagree with me.
Norman Brown, Ph.D., LMFT