With the way you’ve described things, I agree with your friends, it sort of sounds like he might like you too (given the way his friends are acting) but is too shy to make a move OR he could be feeling a little intimidated by you and thinking he’d get shot down.

What if you just walked up and asked him if he’d like to go to a movie this weekend or maybe check out a new restaurant or something?  or if you know you both enjoy or have been meaning to try some activity in particular (like one of those painting classes for example), ask if he’d like to go do that with you?

I think it’s definitely worth a shot. You’re right, it’s 2019 and perfectly acceptable for girls to ask guys out and I know plenty of guys who loooooove it when that happens (it takes the pressure off of them. lol). The worst that can happen is he will say no, and then he will be going to another school next semester anyway, so I’d say go ahead, build up some nerve, and go for it. At least that way you won’t always wonder “what if?”

I really really want to just say “screw it” and just go for itt. I guess the fact that we’re practically strangers makes it very hard!

Right, I can totally understand that, but you might be interested in him for good reason, right? With what you’ve described, you feel some sort of intuitive connection there, so that may be worth exploring even though you don’t know him well yet. You don’t have to go into it expecting a long-term relationship, but rather just a “maybe or maybe not… we’ll see” kind of expectation.

 

But yes I do see your point, if someone takes interest in you and wants to get to know you, why wouldn’t they just do it, especially if we’ve already spoken.

Here’s the question I’d ask….. you have spoken with him as much as he has spoken with you, correct? And you are here, still thinking about him, interested, and wondering if you should ask him out. Who is to say he is not doing the same thing? If this is the case, nothing will happen until one of you makes a move, and the notion that it HAS to be the guy or that if the guy doesn’t make a move, that must mean they aren’t interested is very outdated, in my opinion. Sometimes the guys are just as shy or afraid of being rejected as girls are, sometimes even more so.

So… you can either wait for him to make a move, which he may or may not do, and risk wondering “what if” if he never gets the nerve…. OR… you can make the move yourself so that you can know for sure the “what if” and risk possible rejection. It’s up to you to figure out which risk you’re willing to take.

I guess I’m just trying to figure out if it’s even worth putting myself out there to someone I barely know, or if I should forget and move on!

What are the negatives that you see to putting yourself out there that might make it not worth it to you or how do you think it might effect you afterwards if it turns out he isn’t interested?

Dear Sierra:

I think it is not worth pursuing, so if I was you, I wouldn’t. Your obsessing about him, looking for clues, mind reading, that is wasted energy and using your words, it drives you crazy. So better stop it.

The reason I think it is not worth pursuing is because he wasn’t too shy to ask you questions when he tutored you, you answered pleasantly, it was a friendly exchange and he had plenty of opportunities since to talk with you again, and so, I don’t think that the assumption that he is too shy to approach you is a reasonable explanation to why he hasn’t.

If you find out that you are unable to let go, then approach him at a time when he is alone and ask him what you want to ask him, so to bring the issue to a close, so you no longer wonder.

anita

Dear sierra:

You can practice bravery then (“being brave enough to approach someone”) by approaching him. The practice itself, regardless of his reaction, can benefit you. Do you want to plan that approach, when, what and how you will say to him what you want to say/ ask? If you do, type it here and I will give you my input.

anita

Dear sisi:

When you see him without his friends near by, walk toward him and say: hi, how are you? He says fine, how are you, something like that, and you say: I am fine but I need someone to test me verbally with the subject, will you be willing to test me sometime, when you have a few moments? He’ll probably say yes, maybe he will suggest the time right there and then, maybe tell you that he will get back with you.

Does that reads reasonable to you, to approach him this way?

anita