Interesting non-date locations

He’s cute, he’s funny, and he seems genuinely intersted in what I have to say (however jumbled and incoherent it may be sometimes). He stops on the busy sidewalk on campus to chat, and it’s good times when I don’t freak out and practically run away from him. A mutual friend/coworker told him someone she knows is interested in him. I’m pretty sure he knows it’s me. I’ve taken initiative to go to his office with no good reason other than to say hi. Since then, it’s more of the same. Until last night. I had a dream that I went up and just asked him out. Straight out. I woke up because I was so freaked out by what my dream-self had done, but when I got to thinking about it, I decided it wasn’t such a bad idea. Except, I could never be that bold. I’m not sure what it is about him, but he makes me nervous. I think it’s because I REALLY like him and have so for the past 4 years.

I want to ask him out, but I’m not sure how to do it. I need an event. Something that has other people besides us. Something that is not considered a “date” location. Something that looks as if I just happened to invite him (an “extra” ticket scenario pops into mind).

Here is where all you wonderful people come in. Help me fill in the blanks. Believe it or not, I do kind of want him to say no. Only then can I get over this damn crush already. :frowning:

How do you know each other? Through work? School? Social situations with the multiple friend? Ah, you said “campus.” Why not just invite him to get lunch somewhere, next time you run into each other. After all, you have to eat at some point, and it’s better to have someone to chat with. (Justify it to yourself that way, and also say it to him to “sell” the idea, if you have to.) Take the initiative by saying you know the best little restaurant, and they’re cheap and good and fast… and he’s totally missing out if he doesn’t go with you.

Other than that, what do you have in common? Are there social events on the campus you can go to together? Catch a movie? What about a comedy show at Second City, or an afternoon wandering around the Field Museum? What are you really passionate about, that you’d probably have a good time going to or doing anyway, even by yourself? That would be a great activity to invite him along to, and that way he gets to see you when you’re really alive, inspired, having fun. That is a turn-on for most guys, or at the very least, he’ll have fun by being around you having fun.

I second asking him to lunch, or just “Wanna go for coffee?” They’re one of those borderline could-be-a-date, could-be-friends-hanging-out things that allows him to accept (Yay!) or decline (:() without making a big deal of it. Alternatively, get really drunk and then ask him out. Then, if he says no, you can always blame it on the booze. Actually, I’ve had more luck with the latter suggestion than the former. Maybe I should stop dating drunkards. :slight_smile:

We actually both work at the same university. The lunch idea has crossed my mind but has encountered a few problems - I have a phobic I-can’t-eat-in-front-of-strangers thing. And I think he would think its strange to just ask him to lunch after working (sort of) with him for the past 4 years. Also, when I see him, he’s usually walking home for lunch. Now, if I could convince him to invite me there…

I am all for the boozing up beforehand thing, but it might be a turn-off for him if I show up that way at noon :slight_smile: Maybe a bar thing, but what’s the cover story for inviting him to a bar? I need a cover story so, in case he says no, then I won’t take it as personally.

On the upside a guy gave me his number today without me even asking for it. That’s a confidence boost.

But he’s not a stranger…you’ve known him for 4 years!

In a small talk kind of way…
I’m just chicken. I know what you’re saying makes sense.

One of the nicest friendships of my life began when a young man asked me to accompany him to the zoo. It wasn’t a romantic date kind of thing, but it was interesting and provided many opportunities for conversation.

Just ask him out. No need to be coy. He gave you his phone number. It’s a pretty obvious signal.

Follow Tracy Lord’s lead and take him to Serenity. Granted, that doesn’t open until November, but the time between now and then will give you plenty of time to [del]stress out[/del] prepare.