Making the friend-->dating switch

[jsprplc2006]

Hi - I'm new here! I'll try to be brief...

I'm an Education student about 12 months from graduation, 24 years old, and I've been out since I was 16-19, depending on who you ask.

Two years ago, I went on a "first date" (coffee) with someone I had met online. He was also an education student, and although the conversation went well, I found out a couple days later that his previous (and only real) boyfriend (as of yet) had cheated on him, and he wasn't ready for another relationship yet. I had to pester him to be more explicit, and got the text "I'm not interested in you". It sucked, but I needed it, because I was smitten.

BUT, last September, we started hanging out together on campus on a near-weekly basis as friends, just chatting about whatever we liked. We got to know each other, and although I was in a relationship this entire time, we started opening up to each other about more intimate details of our lives. As these months wore on, I started to detect a little bit of flirt-iness from him around me, although I'm really bad at noticing those things, and I was in a relationship, so I thought nothing of it... until now.

My previous relationship ended (peacefully) before this Christmas, and only two days afterwards my friend told me he was ready to start dating again. I didn't ask at the time, but I fired him an e-mail asking if he was still "not interested" in me. As it turns out, he now IS. And I'm interested in him. So after the two of us went to see a movie on Boxing Day (as friends, not a date), I asked him face-to-face if he'd be willing to go out sometime and see if we could me "more than friends". I got *reasonably* emphatic "yes", although he said we should take two weeks to space ourselves out from my last relationship (I assume was his reasoning), which I agreed made sense.

We're going out to lunch this Saturday (again, not as a date I assume, since our little two-week period isn't up until next Wednesday, but a question has started to knock around in my head:

I've never dated a "friend" before, since everyone else had been a romantic interest from the get-go. So now that I am, I'm unsure just how to conduct myself. I understand the whole follow-your-heart thing, but every other time, the first hug, kiss, etc. just came when we were both comfortable with it. The problem is, this person and I are already completely comfortable around each other, so my compass is confused. I can't just randomly plant one on him!

Has anyone ever been in this situation? I'm just trying to figure out how the whole flirting and/or making moves thing works when you already know the other person well in a different context.

[SolemnBoy]

Maybe I misunderstood the question but since he made the decision that you shouldn't try anything "romantic" for two weeks, then you would probably be wise not to flirt or make a move at all before the time's up, right? Afterwards you can probably be free to express yourself more freely with things like that.

[jsprplc2006]

Yes - you sort of misunderstood, but no worries.

This mutually agreed upon "two weeks" began almost two weeks ago.

My question was, when this time is up, does anyone have any ideas about how I can move things forward without seeming weird, since I have no experience dating anyone I didn't initially meet for that purpose!

[Blue]

Be gentle and tactful but honest.

Something along the lines of "Part of me wants to throw myself at you but, part of me doesn't want to ruin a great friendship if it doesn't work out for us. I'm a bit scared/nervous. What about you?"

Honestly, if you both approach this as mature adults, with an understanding of what past relationships have done to him. (made him a bit skittish) and, talk it out, you won't loose the friendship, you will both know where you stand with each other and, it may very well become more, but it won't be rushed, and if you do become a couple, it might just have the potential to last because you know each other as friends and, for who you really are before jumping in the hay so to speak.

[pellaz]

... I'm just trying to figure out how the whole flirting and/or making moves thing works when you already know the other person well in a different context.

no reason not to do the whole date routine. Yes the flirting making moves works.

[jsprplc2006]

Be gentle and tactful but honest.

Something along the lines of "Part of me wants to throw myself at you but, part of me doesn't want to ruin a great friendship if it doesn't work out for us. I'm a bit scared/nervous. What about you?"

Honestly, if you both approach this as mature adults, with an understanding of what past relationships have done to him. (made him a bit skittish) and, talk it out, you won't loose the friendship, you will both know where you stand with each other and, it may very well become more, but it won't be rushed, and if you do become a couple, it might just have the potential to last because you know each other as friends and, for who you really are before jumping in the hay so to speak.

Very sensible, thank you.

I know that was his primary fear too; when I asked him if he'd like to try being "more than friends", I told him (to quote myself) "I want you to know, whatever becomes of this, you won't lose me as a friend. Unless you hit me with a stick, or throw acid in my eyes, or something like that."

I'm just unsure of what cues I can follow... Because of our personality dynamics, I know I'm going to be the one who has to make most of the advances, and although I'd be perfectly happy to lay a kiss on him on the first "date", I'm terrified of ruining the potential of a relationship. I'm at the point where having him as a partner far outweighs the potential loss of friendship, so my dating compass is quite skewed.

[jsprplc2006]

As an afterthought, the line "part of me wants to throw myself at you" is something I may end up saying myself!

I fall asleep thinking of this guy... I'm *almost* obsessed with him. But I'm afraid if I actually tell him this that he'll think I'm some sort of weirdo and bolt - even though we've known each other for two years!

[Undreamt]

you have been doing a lot of friend type activities together, why not organise a date type activity.
Just a bit more romantic, a bit more personal, Nothing has to happen specifically, It just allows you to change the mood and acknowledge the change in the relationship dynamics.

Maybe get him a small gift (box of chocolates or something).
If you usually split the bill on dinner, offer to pay.
Or drop him home after your date (its probably better to end the date cleanly rather than drifting into friends hanging out territory)

Just make him feel a little bit special and show him you care and i'm sure everything will go well.

Good luck

[jsprplc2006]

Well... we saw each other again today, and for some reason I feel really crappy about it

We had a fun time going for lunch, lots of amusing conversation, but for some reason or other I got the feeling afterwards that his level of interest in me was declining. I feel like I'm going to die if I don't snag him though.

I almost want to find a book entitled "How to Make Someone Fall in Love With You", so I can get this guy, but geez. I can't believe how much control this person has over my emotional state. I feel like if he told me he didn't think we were a good match I'd end up feeling near-suicidal for a month. I'd never actually do that, but I know the feeling, and what can bring it on :/

[jsprplc2006]

Okay, I have a big-time update, and I'd LOVE to have opinions on it! My friend and I went out tonight (neither of us labeled it "a date"), and here's what happened.

So here's the run-down of what happened tonight. We went out for a coffee, and then to see "Silver Linings Playbook".

He made a couple "you're so cute when... " comments - or variations thereof during our coffee. On the drive to the theatre, we somehow got onto the topic of physiques, and he said that for some reason or other he found having a TINY bit of a beer belly, just above the belt, cute. He then reached over under the seatbelt and felt for one on me. I don't have one at all, unless I'm seriously slouching, but when he stopped, I said: "So?", and he replied (with a smirk), "you are ideal."

After we sat down, and about within about 5 minutes of the feature film starting, I got a feeling, and went for his hand. He happily took it, and we spent the remainder of the movie (~100 mins) doing all sorts of "movie-armwrest-awkward-kama-sutra" cuddling, including his head on my shoulder for a good half-hour, and my arm around his neck for another 20. He tried the same on me, but said that sadly I was too tall for it (even though I'm only about 1-2 inches taller than him). During the hand-holding bits, he spent the entire time stroking my forearm/upper arm with his free hand.

The movie ended, as did our embraces, and we talked about the plot on the drive to his house. We spoke nothing of our "cuddling", although when we got in front of his house, I said: "Well, I had a lot of fun... with... the way tonight went, and I'd love to do it again sometime!" At that, he half-smirked, paused for about 2 seconds, and said "If you're lucky." I replied "Okay then, haha, bye!", and he said "Bye!" back.

So - I know I should feel really good about the night... but the "If you're lucky" makes me a bit nervous, I suppose just because it's not what the evening felt like to me. Is this just him playing hard to get? Because that's what I figured... and as such I'm not going to text/call him until he does - or 3 days elapse, whichever comes first.

Does this sound like a good plan, or am I misreading him?

Thanks in advance for your input, guys :p