How do I maximize the odds of a good outcome when I tell my friend I'm in love with him?

April 1, 2009 12:57 PM

I'm in love with my friend. I'm going to tell him, but not for a few months. A) What do I do in the meantime? B) Any dos/don'ts for when I tell him? C) How do I both hope for the best and keep my expectations in check so I don't get hurt if he's not interested? D) Any way I can feel him out for signs of interest?

I'm a woman in my 30s. I've been friends with this man for 22 years. For many of our adult years he was unavailable for dating and so not-an-option that I never gave it a thought. A few years ago that changed. For the past two years or so I have been very much interested in him, in fact, I think I'm in love with him. For various reasons including the value I place on our friendship and the fact that I was dating someone else during part of that time, I have not seen fit to pursue this, but now it's clear to me that this is not going away.

This is both an emotional/physical attraction (I want to be with him) and a sincere belief that by all logical/rational/detached measures we are vary compatible: we she are the same values, want the same things from our lives, see eye to eye on things like money, kids, places to live, family, religion, politics etc.

We do not currently live in the same city, but we talk on the phone maybe 3 times/week and we email almost-daily. I am going to be in his city in 3 months for a conference. After the conference we will spend 4 days together hanging out and I'll be staying at his place. Beginning a few weeks after that we will be living in the same city. I would like to tell him at the end of this trip, just before getting on the plane and heading home. My plan is to tell him over breakfast and then head straight to the airport.

My thinking here is that telling him just before I go will give him some time to think about it before responding. I plan to suggest that he give it some thought, because I think this will be unexpected to him. Even if he knows right away what he thinks, it will be less awkward this way and we can start fresh (as friends or as more) in a few weeks when we're living in the same city again. Also, if I should end up terribly hurt by this, I would rather be alone with my hurt.

Oh, and when I say "tell him" I don't think I intend to tell him that I'm in love with him (title notwithstanding), which would probably be a bit much. I would tell him that I am interested in pursuing more than friendship. I do understand that it's possible we could date for a few weeks or months or years and discover that it really doesn't work. I get that, but I think it will work and I want to try.

His feelings: Unclear. At times I kind of get the sense he might be interested. Occasionally he will say something along the lines of "what I really admire about you is X" where X is something he has told me he wants in a partner. He compliments my appearance/clothing sometimes, but that's also just a polite thing to do so I don't want to read too much into it. He shows a lot of interest in my life. He's said to me "what you need is someone who Y" where A) He's absolutely right and B) Y describes him pretty well. Things like that. But he's also very clueless and so I could absolutely see him sending signals unintentionally, especially since I'm searching for signals. And I could see him not sending signals even if he does feel some attraction or desire for more.

So my questions are:

A) How do I handle my relationship with him up until I see him/tell him?

I think he's unlikely to start dating someone in that time, but he does occasionally tell me about someone interested in him, who he is not interested in. THis makes me feel awkward since I have an obvious conflict of interest that he doesn't know about.

Anything I can do between now and then to maximize the chance that when I finally tell him he will be interested? I feel it can't hurt to make sure I'm as hot as possible when I get there (extra workouts, lots of moisturizing, I'll get my hair done, get everything waxed etc. before I go). I'm trying to be a particularly good friend to him, but in practice there's not a lot to do here. There's only so much you can be "extra good" at chatting. Anything else I should do?

B) Any thoughts on what I should say/how to make my case when I tell him? Feel free to write an actual script. I expect to be stammering and I may need one. Oh, and the classic AskMe advice, get drunk and kiss him, is not an option. I know him well enough to know that it would turn him off even if he were into me.

C) I'm really scared of getting hurt. What if anything can I do to protect or shield myself a little. I don't want to resort to belittling self-talk about how there's no way he could possible be interested in me and I shouldn't hope for anything. On the other hand, I realize that my hoping could lead to some very deep disappointment.

D) Is there anyway short of asking him to find out if a clueless man (too clueless to send or receive subtle signals, trust me I know this from many other things I know of him) is interested in more than friendship? If I try feeling him out and it seems he's not interested, should I drop it or tell him anyway?

E) Other thoughts or advice that I may not have thought to ask are welcome.

Sorry for the length of the question, but that's hard to avoid with anon questions, I guess.

throwaway email: [e-mail]

posted by anonymous to human relations (42 comments total)

I wouldn't wait. You'll drive yourself crazy hoping he doesn't meet someone new.

You can't protect yourself from being hurt, but at worst, you won't be any worse off than you are now, after you get over the blow to your pride. And at best, he thinks about you the same way.

I'd just, you know, call him to chat. And drop hints that maybe you'd like to go on a date when you see him next. It should become clear quickly if he's into the idea of going on a date, or not. And if the answer is "not," then you aren't there to be embarrassed. And if the answer is "come on down," then hop on the next train.
posted by musofire at 1:00 PM on April 1

A subtle tactic may be to task him with finding a restaurant for you two to go to on your last night, and if he asks what kind of restaurant you can suggest, "romantic" and see how he responds.
posted by rhizome at 1:03 PM on April 1 [4 favorites]

If you do wait, tell him at the beginning of the 4 days, not at the end. If he IS into you, he'll be grateful to have had that time to explore what this is going to mean. If he's not into you, you can always come home early or spend the time by yourself. I don't think it's fair to drop a bomb like that on someone and offer no time for them to figure it out with you before you vanish; you may be shooting yourself in the foot by leaving.

I actually agree that you shouldn't tell him till you're there though, because if you do, both of you will have months to overthink and over-anticipate your upcoming meeting, and then it won't feel natural when you actually end up face to face.
posted by hermitosis at 1:10 PM on April 1

I don't think a friendship that's lasted 22 years would have trouble surviving this in the meantime. I would tell him now, after all, there's always a remote chance he could meet someone else in the interim.
posted by delmoi at 1:13 PM on April 1

Going out on a limb here, if you two see eye to eye on so many things, and there is an inkling that he could possibly be interested, why has there been no action on his part?

It very well could be that you two live far away from each other. If you are prepared to drop the love bomb on him, you should also be prepared to make the relationship work. LDR's are fine, but your shared values of kids, family, and places to live don't lend themselves to that.

Your post doesn't really mention the future with the exception of possible acceptance/rejection. And to get at the answer you need, thinking about the future after that is important.

Best of luck.
posted by munchingzombie at 1:14 PM on April 1

D) Any way I can feel him out for signs of interest?

Careful here. If he picks up on what you're doing and calls you out, are you prepared to broach the topic via phone/email?

If no then I might go easy on that point.
posted by Smarson at 1:14 PM on April 1

Yeah don't tell him. Either be patient and accept that he might slip away from you again, or get your ass out to his town now "unexpectedly", get drunk with him, and smooch.

I did this and spent a year being really happy. It all ended in heartbreak, of course, but it was eminently worth a try and I regret nothing.
posted by Potomac Avenue at 1:16 PM on April 1 [1 favorite]

A. I think that you just have to go on like you have been going on, suffering (or feeling those feelings) in silence. I have been in that position, vis a vis a lifetime friend. Many years, in after waiting for it to morph into something else, I finally came out with it, and found out that this was the furthest thing from her mind. We are still friends, I still have those feelings, somewhat, and we don't go there.

B. Just come out with it, at a time when you do not have to spend a lot of time with him afterwards. If he responds in the positive, there will be plenty of time to catch up, but if he is not on the same page as you, I think that you'd want to get out of his presence asap.

C. Nothing for that. You may very well get hurt. I hope it comes out like you want it.

D. I do not know of any way you can get advance signals. Please let us know if you come up with anything along those lines.

E. You might, with a bit of alcohol in you both, and at the right moment, say, "gee, I was just wondering what would happen if I tried to kiss you right now," and see what happened. If he kissed you then, he'd get the "vibe" of your feelings towards him, likely better than if you'd expressed those in words. . .just a thought.

Good luck. . .I hope that it goes your way (and that he's into you).
posted by Danf at 1:21 PM on April 1

For godsakes don't tell a person you've never been on a date with, never made out with, never had sex with, never gotten drunk with, that you love them.

Look, if you like this guy, make a play. Be direct! Say to him, "Hey, do you ever think about us getting together?"

But don't come out of the gate saying, "I love you." That's weird, and creepy, and clingy, and gross, and stalkerish... ugh.
posted by wfrgms at 1:22 PM on April 1 [2 favorites]

Seriously, just ask him right now.

Don't "drop hints" or make vague implications. Be straightforward about what you're thinking.

If the shoe was on the other foot and he was having these same feelings for you, wouldn't you want him to tell you? Would it really matter exactly what he said?
posted by hamsterdam at 1:26 PM on April 1

Thirding tell him now. I think you're on the right track with the not jumping right into the "I'm in LOVE with you" bit, more along the lines of "Hey, I'm glad we've been friends for so long and I think I like you like you." Or you could try flirting more. Not in an awkward or unnatural way, but something that gets his mind thinking "maybe she likes me..."

In any case, the only way to protect yourself from getting hurt is to not try. Which hurts in a different way when they've moved on and you've blown your change through cowardice and inaction. I think we've all been there. So take the chance. And by telling him now, if he isn't interested, it gives you some time and space to work through it. I don't know if he likes you romantically but he obviously likes you a lot to be your friend for 22 years and talk/email so frequently.

Good luck!
posted by 6550 at 1:26 PM on April 1 [1 favorite]

I'm really scared of getting hurt. What if anything can I do to protect or shield myself a little.

comes with the territory. Just tell him now. Alcohol will help.
posted by Ironmouth at 1:29 PM on April 1 [1 favorite]

People, of course she's going to make a move on him! She's asking How and When.

Kiss, don't talk. It's just as hard to make yourself do and 98% more likely to work.
posted by Potomac Avenue at 1:34 PM on April 1 [2 favorites]

yea, don't wait - ask him in a nice simple way "hey, we've never been single at the same time before, want to try dating?" If he's not into it, then you can carry on as usual, and you'll be over it by the time you are in the same city as him, and you don't lose the friendship. On the other hand, if he says yes, visit as soon as you can! It's totally worth the risk - The best relationships I've had have been with guys that were my friends first.
posted by 5_13_23_42_69_666 at 1:40 PM on April 1

Like all the "don't wait" people I'm saying "don't wait." Tell him you're interested in adding a romantic component to your friendship and ask him what he thinks about that.

I would like to tell him at the end of this trip, just before getting on the plane and heading home. My plan is to tell him over breakfast and then head straight to the airport.

This seems like a really odd plan to me. 'OH BY THE WAY I'D LIKE US TO BE ROMANTIC PARTNERS AS WELL AS FRIENDS GOTTA GO BYE' is not really how grown-ups do relationships.
posted by Sidhedevil at 1:46 PM on April 1

--Occasionally he will say something along the lines of "what I really admire about you is X" where X is something he has told me he wants in a partner.
--He's said to me "what you need is someone who Y" where A) He's absolutely right and B) Y describes him pretty well.

It's possible that a relationship with you has definitely crossed his mind as well. Sounds like he could be interested, and has held back for the same reason you're holding back....out of respect for the long friendship.

--Beginning a few weeks after that we will be living in the same city.

I'd really like to know how that came about.

wfrgms said: For godsakes don't tell a person you've never been on a date with, never made out with, never had sex with, never gotten drunk with, that you love them.

Dude, she's known him for 22 years. Stalkerish? Come on. She's much more intimately acquainted with him than someone who's gone on 3 dates with the guy.
posted by iconomy at 1:52 PM on April 1

followup from the OP

On why nothing has happened yet if there's some possibility he's interested: We have lived in different cities for most of our adult lives with at most a few months here or there in the same city. For much of our adult lives he was unavailable for dating. He was not seeing someone else, but he was not datable (by anyone). I don't want to say more than that. I've been seeing other people for about half the time since he became available for dating. I had hoped this attraction would go away because I am scared to lose a friend but since it hasn't, I decided to tell him.

And again, I'm going to tell him that I'm interested in pursuing more than friendship, not that I'm in love with him. I totally agree that telling him I'm in love with him would (rightly) freak him out. Hell, I get freaked out when guys I'm actually dating tell me they're in love with me!

Right now we are very far apart and it's more of a 12 hour plane trip kind of thing than "hop on a train."

And though I didn't bring it up in the question, because it's weird since we've never gone out as someone has already so delicately pointed out, I have thought about the future: House, dog and a couple of kids. But mostly I try not to think about it because there's no sense at all in getting my hopes up. One step at a time. We need to find out if a first date goes well, or happens at all, before buying a house and picking out the living room curtains.

Thanks everyone so far. I will consider other plans on when to tell, but I have a lot of trouble imagining doing it by phone. And since he's moving so far from his current location pretty soon, I also have trouble imagining that he would get into any sort of relationship there now.

posted by jessamyn at 2:18 PM on April 1

wfrgms: The OP said she isn't going to say "love," she just wants to get an idea of where he stands. Having said that, your line "Do you ever think about us getting together?" is a great one. The important thing, after all this wonderful/terrible anguish is to get a really clear idea so you can either progress with an open heart or go and hide and lick your wounds with a reasonable explanation. Both are fine outcomes because both will let you get on with your life and finally know the truth.

If you'd rather ease into it and foreshadow the "telling" so his jaw doesn't hit the floor: you could lean your head on his shoulder as you walk together (or if you're several inches taller than your love interest, as I am, you could hold his hand or touch his bicep as you walk together on the street). I know that can be a little weird with long-time friends though, especially if you're not usually a touchy pair.

I'm getting carried away and so I'm going to write a little script here. I imagine this happening during a phone conversation.

The guy (complaining): "Susan from accounting asked me to go on a date with her and I don't think I'm interested."
The OP (feeling awkward): "Umm, yeah... that's a tough one."
The guy: "She just doesn't write AskMeFi posts that are adorable enough. You know what I admire about you, OP? You're so open-hearted."
The OP (jokey): "Maybe we should go on a date!"
The guy (not getting it): "Ha ha ha..."
The OP (bold): "Heyyy there's an idea. Have you ever thought about it?"

Also, I'm going to e-mail you because I NEED to know the outcome of this situation.
posted by cranberrymonger at 2:23 PM on April 1 [1 favorite]

OP followup: He was not seeing someone else, but he was not datable (by anyone).

I don't know what this means, but tread carefully and listen to him if he tells you he can't be in a relationship for emotional/psychological reasons.
posted by cranberrymonger at 2:27 PM on April 1 [1 favorite]

He was not seeing someone else, but he was not datable (by anyone).

If this is because he was a priest/monk/other religious, or if this is because he was following a religious path that was anti-dating, there are a whole set of complications particular to these issues.
posted by Sidhedevil at 2:31 PM on April 1

He was not seeing someone else, but he was not datable (by anyone).

If this is because he was an addict, or if this is because he was in jail or a mental institution, there are a whole set of complications particular to these issues. I don't mean to make light of this, but going through a time where someone is "not datable" to me is a really big detail that should have a lot to do with how to proceed. Everyone will jump to their own conclusions about what that might mean, that's my conclusion. Being coy about this in an anonymous question also seems to me to be a bit of a red flag that there's more to this story.
posted by jessamyn at 2:39 PM on April 1 [1 favorite]

I'm a romantic person at heart, but a long-distance relationship is hard to maintain without a lot of visiting (I know, I've been there). What are you hoping for if you do end up dating, in terms of the immediate future (not long term house, dog, kids)? What s the ideal short-term outcome? What's supposed to change between you that makes it dating and not just friendship?

If you are serious about dating him then are you willing to move and be with him soon? Bring up the idea of moving closer to eachother distance-wise. I think parts of this can be discussed with him without being too obvious. Get a feel for what he thinks on long-distance dating and how it would go. Even if a relationship isn't a guaranteed thing, moving closer couldn't hurt the friendship - you've already known eachother so long.
posted by lizbunny at 2:58 PM on April 1

I'm going to go the other direction on this one - wait until you are living in the same city.

There's going to be a whole different reality when you are both living in the same city - why not see how to approach this at that time? You two can spend time together/hang out, and at some point, if it feels right, you can tell him - "hey, we've never both been available at the same time - I wonder if it would be weird if we thought about going on a date together?" You can see how he reacts (which you can't as much if you tell him at the conference), and you won't have the pressure of a deadline to talk to him about it - you both live there, you can do it when it feels right.

I am concerned about the followup, I'm not gonna lie. You know better than I do - but if there's reason for you to be cautious, then please do.
posted by KAS at 3:02 PM on April 1

lizbunny, the OP says "beginning a few weeks after that we will be living in the same city." -- that being the meeting in which she'll tell him she's interested. So the long-distance relationship issues don't really apply.
posted by kate blank at 3:04 PM on April 1

If this is because he was an addict, or if this is because he was in jail or a mental institution, there are a whole set of complications particular to these issues.

Holy crap, I hadn't even thought about any of that.

I don't mean to make light of this, but going through a time where someone is "not datable" to me is a really big detail that should have a lot to do with how to proceed.

Yes, this. All the things that could potentially make someone "not datable by anyone"--religious commitments, psychological/emotional turmoil, addiction, incarceration, serious illness, a commitment not to date until one has completed gender transition, other things I'm not thinking of--are going to make a big impact on how one chooses to pursue subsequent relationships.
posted by Sidhedevil at 3:23 PM on April 1 [1 favorite]

follow-up from the OP

There are no psychological/criminal/medical issues here. I do not want to post the details because they would make the question (and me and the guy) easily identifiable to at least one MeFite (not the guy in question). Suffice it to say that while everyone and every relationship has its own unique issues, the non-dateableness was over several years ago and the situation is effectively resolved/over and any emotional issues he has about this period of his life have been resolved, insofar as one ever resolves issues about periods in ones life. Really, there are no red flags here. I swear it.

posted by jessamyn at 3:43 PM on April 1

Definitely tell him BEFORE the breakfast of the last day. I have no patience so I would tell him now, but if you're sure you want to wait until you see him, do it the first or second night - have a few drinks (not enough so he just assumes you're drunk) and flirt a little and just tell him.
posted by KateHasQuestions at 4:19 PM on April 1

Hmm, if he was a priest who left the fold, you may have a whole other set of issues to deal with having to do with sexuality...

(And pardon my mind for jumping there -- I actually know someone like this!)

I agree with those who say, tell him at the beginning of your visit. Otherwise the knowledge of what you're planning to do is going to be constantly on your mind, coloring your interpretation of his every small gesture/throwaway comment, and generally twisting your experience of y'all's time together.

If you are such good friends, and you admit you'd like to try something more only to discover that he's just not into it, your relationship CAN and WILL survive the awkwardness.

That said, thinking strategically here, I agree with those who said a kiss might be the best way to ease into this conversation. If he's shocked and pulls back, you can say, "Oops, lost my head there. Sorry. Are we cool?" and brush it under the rug. If he startles and then kisses you back, you can let the conversation... develop. Later. :)
posted by artemisia at 4:37 PM on April 1

PS - By sexuality, I mean "a whole lot of guilt having to do with reentering the world in which I am allowed to act on sexual desire."
posted by artemisia at 4:38 PM on April 1

I am in the group that thinks you should bring it up now! Now now now! I know I would be completely anxious about him meeting someone between now and my trip. Unfortunately, it does happen.

I am also in the group that says when you get there - kiss him. I followed the great mefitey advice myself earlier this month and it worked out great! (So far) :)

I am not in the group that says drink.

That's about all I have other than Good luck!
posted by MsLgean at 5:15 PM on April 1

By this month, I mean March. Ugh.
posted by MsLgean at 5:16 PM on April 1

i did this, more or less. after debating for a while over how to tell him, we went out for a 'friendly' drink, i made a move, and you can guess where it goes from there. i mean, it wasn't an accident- i wanted it- but i was really nervous, that's where the alcohol came in. anyway, we ended up dating for about a year then broke up. (i broke up with him.) but i'm glad i did it because if i hadn't, i know i always would have wondered "what if?"

so my advice to you is go for it- in person- and if you need a few drinks to get the ball rolling, why not? however, i would urge you to try not to get too caught up in idealizing this situation. sometimes people who are perfectly suited to each other as friends don't work as a couple. it took me a long time to realize this and it really threw me for a loop, but i ultimately figured out that all me and this guy had was a great friendship. it just didn't translate. i think part of it was that i had spent such a long time looking at him through the friend goggles, that there wasn't any sexual chemistry. sure, there was sexual tension when we were friends and both dating other people. but once we were actually together . . . meh.

i guess what i'm saying is, by all means give it a shot. but don't get so caught up in the idea of it that you forget to be realistic if it isn't working. good luck.
posted by lblair at 5:16 PM on April 1 [1 favorite]

Your plan sounds fine, except for telling him right before leaving. If you're going to be spending four days together, it'd probably be better to bring it up right before leaving.

If you've known the guy for 22 years I think a lot of other things go out the window. I don't think you have to make a move right away or anything like that. I think you can just sit down with him and talk to him about your feelings. It might be easier in a park.

It just strikes me as a little hard to shift gears immediately from friend to something more after having known each other for so long. With that in mind, it seems a little unrealistic to have a few drinks and try to "get together" with him.

In the meantime, if he happens to meet someone else then you can speed up your conversation. Otherwise, waiting the three months doesn't seem to be too long.

Good luck.
posted by fantasticninety at 5:16 PM on April 1

I'd definitely bring it up by phone before you go out there. If you've known each other for 22 years and talk several times a week, surely you should give him some time to think this idea over rather than springing it on him during a visit. And it will be much easier to keep your tone casual if you broach the subject first by phone or email. Toss the idea of dating when you move to his city out there and see what he does with it. I'm guessing the only reason you're holding off is because you suspect he's not going to be into the idea, and you think it will be easier dealing with that when you're back home after the visit instead of before.
posted by MsMolly at 5:37 PM on April 1

There are a lot of men for whom a woman initiating a romantic relationship is an automatic turn-off. For these men, there is a "thrill-of-the-chase" that is a necessary element of the beginning of a romantic relationship. If your friend is one of these men, any overt strategy of telling him you want to pursue a romance will rule you out as a romantic partner.

To be on the safe side, I would suggest you create a situation in which you can plausibly deny any romantic intentions, while at the same time making it a no-brainer for him to make a first move if he is interested.
posted by jayder at 6:35 PM on April 1 [1 favorite]

If you tell him you want more than friendship and he is not interested in you, there's a pretty strong chance the friendship will not survive. It almost certainly will not survive.
posted by jayder at 6:37 PM on April 1

To just clear up what I wrote earlier, "it'd probably be better to bring it up" sometime during your stay and not right before you leave.

Keep in mind how long you've known the guy for - 22 years. I really think if you tell him your feelings in a simple way (I care about you, I'd like to see if this could go somewhere) then you've got your best shot of seeing if it's going to go somewhere legit.

It probably wouldn't take longer than about 10 minutes to share your feelings. It might take him a little longer to respond as you've had a lot longer to prepare your side of things than he has.

Again, good luck!
posted by fantasticninety at 6:48 PM on April 1

Kiss him. Talk is for suckers. Just kiss him on the face.
posted by argybarg at 8:10 PM on April 1

If you tell him you want more than friendship and he is not interested in you, there's a pretty strong chance the friendship will not survive. It almost certainly will not survive.

eh, not necessarily. but it will probably be plenty awkward at first, and it could take a long time to get back to normal. it will certainly be a different ballgame for you. and you might, once the possibility of a romantic relationship is killed, and you're not idealizing him and yearning for him and all that, realize he's not that great. i may be projecting-much on my own history, but there you have it.

i agree you should tell him sooner. because! there is definitely the possibility he will meet someone else in the next few months. murphy's law! it is law.

you should get it over with. can you see him sooner?
posted by apostrophe at 8:39 PM on April 1

A few disconnected thoughts.

1. Keep it low-pressure, casual. On BOTH OF YOU. Which means, on him, don't announce "I'm in love with you." Just ask him out on a date date, and make it clear it's a date date. High pressure stuff scares people.

1.5 And for your own sake, if you make it high pressure on yourself (as you seem to be doing, with your beliefs about compatibility and so forth -- which you don't really know even as long as you've known him, because dating is v. different from friends), you'll start acting funny -- everyone does -- and scare him off, as well as make yourself miserable. So KEEP IT CHILL.

2. The "kiss him" approach has some merit if you think he's attracted to you. Lots of merit, even. In the right moment, e.g., at some moment when you're spending time alone w/ him, there's been lots of touching, etc. You know, signals and stuff.

3. Ignore the people who say this could ruin the friendship. I've had lots of romantic rejections on either end that haven't lead to destroyed friendships.

4. Timing (by which read: "switfness") is everything, but this isn't something that should be done long-distance. A long-distance declaration of romantic interest cranks up pressure, which is bad see #1.
posted by paultopia at 11:25 PM on April 1 [2 favorites]

Too much thinking, too much talking! Flirt a little on the phone for now. Act more or less the same but a little more flirty, casual stuff like "you know what I like about you?" and "I'm excited to see you, let's eat an entire pizza and watch Lost."
Next time you see him, get a wee bit affectionate. Ramp it up over a few hours. A long hug hello. Grab his arm when you cross the street, etc. Nothing too intense, but let your touch remind him you're a lady. Do the side-by-side thing (press up close) in a cab or watching a movie, and see if he ramps up too. If he doesn't back off a bit and flirt more. If he does, awesome, make lots of close eye contact, slow down the conversation, giggle a little, compliment him a bit, then when the mood is right, smooch. Wine first if that's your thing.

Very important: no declarations of feeling until he does it first, which will probably take weeks. No "in love" talk at all, unless he does it first. Let the man lead with the emotional stuff. I know, we're feminists and stuff, but people like ideas more when they think it's their own idea, and love is no different. Remember you don't know if it's really love until you know the lovin's good, so HOLD OFF on that stuff, rein in your thoughts if possible, too. In a few months you can tell him about your feeelings.... Maybe. Play it cool and go get'im, cowgirl!
posted by pseudostrabismus at 10:50 AM on April 2 [1 favorite]

I'll add: when it's time for that very first round of smoochin', your job is not to smooch, but rather to make your mouth available and then wait. Let him smooch you. Don't go jumping on his face or anything. Your body language & eye contact should encourage him to kiss you, then he gets to feel like a total champ when he takes the hint & goes for it.
posted by pseudostrabismus at 10:52 AM on April 2 [1 favorite]