Like I don't want it to be a date-date because that's risky. Just sort of like a friendly way to go someplace together like the movies.
But I'm not really sure how to bring the topic up.
Most Helpful Guy
Do this - it will always work:
Just talk to him at first, but, later in the conversation, let him know of some problem you have (it doesn't have to be a real problem), but it has to be the kind of problem he can fix for you and where you are both together as he fixes it. He will likely offer to come over and fix it. However, you can also make an offer to him - if he comes over and fixes it, then you will make him dinner or something that will 1) make it worth his while and 2) will involve both of you. So, when he is actually with you doing whatever fixing is necessary, that is the date that is not a date. It's definitely a way to have one-on-one time and get to know each other. Before the fixing "date" is over, if you like the guy, then hint at a future date. (That could be the reward for doing the fixing.)
I actually did this in 1990 and met the woman I wanted to marry and we dated for 17 months until she ripped my heart out and left me for ruin.
Watch this episode of Everybody Loves Raymond and watch what Debra does... She uses this classic technique.