How can you fit asking someone out into a conversation?

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Hello, insightful WPers, I have a hypothetical question for you. Sorry if this has been asked already, but I haven't seen it since I joined here in March. If my question has already been addressed somewhere, please direct me to the link!

Suppose you're attracted to a friend of yours and you want to ask them out. This is not a hopeless crush from afar: you've known them for several months and feel very comfortable talking to them--you both can talk for hours and still feel like you have something to say. You were attracted to them from the time you first started talking to them, and you suspect that they were flirting with you from the beginning as well. However, you started out as friends because you were in a relationship when you met them and were not able to break up immediately. (They did not know you were in a relationship until a few weeks into their acquaintance with you, when you became facebook friends with them. While you were still in the relationship, you saw them only for lunch or coffee and were careful never to do anything that might be taken as flirtatious). Right now, you are single. They are as well.

You think they are also interested in you, but you're not 100% sure. They make very intense eye contact with you and engage in flirtatious banter; however, they have never touched you or engaged in unambiguously flirtatious behavior with you. You have had dinner out with them, but there were no unambiguous signs that it was, in fact, a "date." They held the door for you, were slightly quieter than usual, and asked you more questions about yourself than usual, and it felt kind of like a date, but it was never openly stated by either of you during or after. (You also split the bill). You have seen them since, although not in a date-like context.

You have been afraid to ask them out for a while because you only want to date someone who can handle your diagnoses and all the aggravation that comes with them. However, you have gradually off-handedly mentioned atypical things about yourself without directly saying what diagnosis you have, and they seem to like you anyway. You think they would continue to want to associate with you even if you were to disclose fully. You have been waiting for them to make a move for the above-mentioned reasons, and because you are afraid of being rejected or having the relationship not work out, but you've gotten tired of this.

In regards to their own neurological status, they seem to be quirky, but they are not diagnosed with anything. If they are non-NT, they would be higher-functioning than many NTs, and certainly much more so than you are. And as an A student at a good university, you're very high-functioning on paper.

After all this build-up, here's the actual question: How can you fit telling someone you like them and want to go out with them into an ongoing conversation? I just can't figure out how one would segue into this. I don't know how to ask someone out because I last did so in 8th grade, it involved passing notes in the middle of class, and I was politely turned down. I have been in relationships since, but I did not initiate them. More likely than not I would not be turned down, but I'm still afraid. Thanks in advance for your thoughts!

You could really slip it in anywhere, but if you're nervous, one way I find helps is to wait until the end of conversation, as you're having to leave, and just double-back, and mention casually as you're leaving "Oh, and I was just thinking, would you like to go out on a date sometime? Maybe we could ...<insert date idea here>?" ... Or just the first sentence of that, if you'd rather he pick the date. Either way works. =P

Interesting idea. Slipping it in off-handedly at the end would certainly be easier for me.

On the other hand, what if he wants to talk about it more and I've just walked away? Would this strategy be perceived as awkward, or only if I do it wrong? Hmm.

Don't do it when you have to go imminently. Just do it when you're leaving casually. Then if he wants to talk about it, you've already gotten the main trouble of mentioning it in the first place off your chest, and the worst that the rest can hold is him turning you down. As such, you go back and talk to him about it when he asks.

Just remember, sooner is typically much better than later.

Hmm...the trick may be leaving before I imminently have to, then...

"Just remember, sooner is typically much better than later."
Sooner in the conversation, or sooner in my relationship with the person?

Ah, not in the conversation. That doesn't matter much at all that I've noticed. In the relationship. Things can come up and get in the way. It's always better to beat those circumstances to the punch. =P

Yes though, I would recommend starting to leave a little bit before you absolutely must. Say, maybe ten minutes, to be liberal with it. Fifteen if you're feeling really nervous about how long of a conversation you might make of it.

"The Cuban missile crisis was the event that brought the US the closest to nuclear warfare with the Soviet Union during the Cold War and by the way would you like to go on a date?"

lmao.....nice one

LOL, awesome, Book Noodles. Good point though, there's no non-awkward way to say what I want to say, so might as well be funny about it.

[quote="book_noodles"]"The Cuban missile crisis was the event that brought the US the closest to nuclear warfare with the Soviet Union during the Cold War and by the way would you like to go on a date?"[/quote]

I [i]like[/i] it.

Thank you Subtle, right?

If the conversation is going well, it doesn't hurt to just ask [invite them somewhere] once a level of familiarity is established between the two of you. After all, approaching/talking to someone is the hardest step right?

Just don't do this:
[youtube]http://www.youtube.com/watch?v=jRbkkqZikx4[/youtube]

lol. That video is hilarious! I used to love watching Mad TV.

Keep in mind, we are friends and we do stuff together, so just saying "let's go to a movie/play/whatever" might be too subtle, as Dellingr pointed out. The point needs to be that I'm asking to do something because I want to be more than just friends (as much as I hate that expression). Kind of annoying, because word choice is a lot less problematic for asking someone to hang out with you than for asking them for a date. You've had some amusing ideas so far, and I hope I'll hear more from people who've asked someone out successfully.