Here's one that will take a long time

[Zen]

I don't remember...

[mimitabby]

I don't remember...

yeah, tell me about it.
(married 30 years, never "dating" again)

[Geonz]

I wish somebody I knew could be a fly on the wall - I would gladly (okay, not *gladly* ) file this under "friends" if, indeed, that's what it's meant to be. We're each, however, just socially unique enough so that it's harder to read each other. I paid a completely gratuitous visit to the LBS and we had a lovely time folding and unfolding that Dahon Any flies on the wall, however, have not spoken to me about what it looked like to them
Suggestions that we head soemwhere after a ride, etc. have generally gotten "too busy" negatives. It's been a while since he asked me out - we did several concerts together a while ago, but not as dates. However, since we communicate a lot more now than we did then - he lets me know when he's going out of town, as well as at least *some* stuff happening in his life, and oh, what he thinks of this or that article in the New York Times as it relates to life and death and the pursuit of happiness - I suspect/hope that's because if he asked me out now it would be a date.
Suggestions don't have to have anything to do with anything like dating - I'd like to be creative!

[BleeckerSt_Girl]

Geez this seems awfully complicated! If you have communicated so much with him already....why don't you just ask if he'd be interested in exploring a romantic relationship?
Worse that could happen is that he'll tell you yes or no- which is what you want to know, right?

[Zen]

Lisa has a good point. Sometime guys are either just a little dense or frozen with fear.

[Starfish]

Suggestions that we head soemwhere after a ride, etc. have generally gotten "too busy" negatives. It's been a while since he asked me out

You know, I hate to say it, but if he isn't taking you up on offers to do stuff together, I'm thinking he might not be smitten...

But, don't listen to me, I'm an idiot.

[teigyr]

Hmmm. I will have to ask DH what he thinks but rest assured that names will be changed to protect the innocent.

My initial reaction is that some guys (DH included) are semi-dense. It's not an insult, it just is what it is. You have to be blunt and put it out there or else they don't notice. I also know, however, that some guys know when you "like" them and instead of dealing with it (ie acknowledging it and saying they don't feel the same way or simply acting on it), they act like scared little bunnies. Not to be judgmental, women do it too Speaking for myself, if I feel pressure, I act in non-dignified ways.

So, p'haps if you two went out as friends and you asked "have you ever thought...." in such a way as to not make him feel horrible if he said no and your friendship was left intact. While initial impression seems like if he was into you he wouldn't always be busy but then again, you never know. I have had male friends that I had THE hugest crushes on and bailed out on "let's hang out" not-dates because I didn't feel like it or was tired but had I known they liked me, I would've gone for sure.

Lastly, maybe he never DID think about more but it's not to say he wouldn't if it were to be brought up.

So in a roundabout way, I think I covered all the bases and answered nothing. I think though if he hasn't understood subtle by now, it's time to step it up a bit as long as it's in a non-pressured way. I'll see what DH thinks though. While he'd never post here, this is one of the times where a male perspective might be warranted. I will report back.

[KnottedYet]

I am socially inept. Kinda like a guy. (but cuter ) If I had a crush on someone and they asked me on a date, I'd panic and say "no." (even though I wanted to say "yes")

So... maybe you shouldn't take "no" as an answer. Or maybe you should take the whole question out of the realm of words. (but slowly, so as not to frighten the timid wild creature)

[Tuckervill]

But don't put all your hopes in the one basket. It could ruin a beautiful friendship, if he perceived you as desperate--or more likely, made him terrified to hurt your feelings by saying no (most guys worth their salt are terrified to hurt someone's feelings and it could make him panic and avoid you for a long time). I wouldn't force a date on him, either, with the dressing up and all that.

Just bring it up in conversation. Be who you are. Be true to the relationship you've already built.

Karen

[Zen]

So in a roundabout way, I think I covered all the bases and answered nothing.

How about this-
would you rather regret something you did do or something you didn't do?

[lph]

aaah - I had that as my guideline for a while - and let's say I certainly regret some things I did... If you're somewhat the reckless type, you'd better have a bad memory.

Joking aside, I think Tuckervill put it beautifully. You have to be true to yourself and the relationship that's already there. I'd say skip all the careful flirtation if you're actually kinda sick of it. If you can be honest and straightforward without seeming desperate I'd say your chances are good of both getting an honest answer and keeping him as a friend. You want to tell him you're interested, but also that you're not going to shrivel up and die if he says no.

But it would help if you were somewhere conducive to this kind of conversation. And yes - some of us put this a lot better in, uh, body language than in words.

Scary stuff, this. But hey - it's what makes the world go round, right?

[teigyr]

How about this-
would you rather regret something you did do or something you didn't do?

That makes my head hurt. I had an initial response but then thought more and wafted and then thought more and went back to my initial. It's early

DH was about as circular as I am. He says the variables are: he knows and doesn't feel the same way, he knows and DOES feel the same way but doesn't know how to initiate it, he's thought about it but doesn't know your feelings (and his are either pro or con), and he has never thought about it.

DH thought it could be brought up a few ways that would allow the relationship to stay intact. One way could be "hey, have you ever thought about..." or the more evil way of setting up a story of "I was talking to <insert name here> and were discussing the perfect traits in a person I'm dating. I kept coming back to you. Have you ever thought of...?" I don't like the second way because I'm bad at making up stories. DH thought the R word (relationship) could be brought up because there is a relationship already.

I think no risk no gain but you have to be prepared for all eventual outcomes. For me, at least, the known is generally better than the unknown.

Good luck though and please keeping posting as to what happens! Re the "accidental" physical contact...I keep thinking of the H.S. days. You know, when the guy yawns and puts his arm around you or the old "I have to roll up the car window" maneuver. Then again, I guess most car windows don't "roll up" anymore