Hoping Virginia Really IS For Lovers

Dear Dating Medic,

This may fall into the category of "how to make the transition from friend to something more," but its a bit more complex than that. I've known this guy for 4 years now, and from day 1, we hit it off - banter back and forth, attraction, etc. - even a few dates (after my friend that introduced us got over the fact that he wasn't interested in her). Then it kind of fizzled - but not in a bad "I can't believe he never called" again way. Truth be told, I didn't really think much of it. Fast forward a few years ... I've dated a bunch of guys in the meantime, and he has too (um, girls, obviously). We are still friends. We see each other at social events once every six months or so, and every time we see each other, we pick up right back where we left off, and things are great. Then we continue to talk for a few weeks after that, and then it stops again. The last time I felt like he was trying to gauge my interest, I was dating someone, so obviously I didn't reciprocate anything. When he found out that I was going to be in San Fran for the 4th of July, and he was too, he made plans to stay a day longer and go to a baseball game with us.

Blah, blah, more details than you need to know, surely, so I won't continue. Bottom line: last time I ran into him, a couple weeks before Christmas, something was different, and I can't stop thinking about it. A mutual friend invited him to go to the temple Visitor's Center (in DC) right before we all took off for Christmas, and he came - but not after contacting me about it. We, of course, had a great time together. Which naturally makes it that much harder for me to stop thinking about the giant "what if" question.

The real question is how to broach the topic without actually broaching it, and without making myself that completely vulnerable. No one wants to do something they feel forced into doing (he especially, we have had that conversation) - and not that I feel like I would be forcing it, but still. Its always better when its HIS idea. I just need to figure out how to send out the vibe that makes him think along those lines, and not let the "but we have been such good friends for so long that something should have already happened by now" or "she is only interested in me as a friend" lines of thinking take over. I kind of think that we've both thought about it but neither of us wants to be the one to bring it up.

Oh, and to top it all off, as if I hadn't been thinking about this situation (which I fully realize is only really a situation in my head right now), when I woke up this morning, I had a text from him (this is the first communication we've had since before Christmas, so it is kind of out of left field) ... "Happy new year! Are you excited? This is our year of thirty :-)" Hmmmm. Now what?!

- Hoping Virginia Really IS For Lovers

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Dear Shanna loving in Virginia,

On the subject of Love, may I first mention to all the singles out there on a non-related topic, we're approaching Cupid's Window! Cupid's Window, for the uninformed, is that window of time before Valentine's Day that adds its own unique pressures and possibilities. If you continue dating someone or meet and begin dating them from now until usually about a week and a half before Valentine's Day, we have an automatic DTR (Defining The Relationship). If you've had any meaningful and frequent dates within this window, Valentine's Day will tell you where you stand. Like Christmas and birthdays, V-Day takes us to a new level of the symbolism of commitment and it's full of free clues if you keep your eyes open. The way that he or she- especially he, since it's basically a girl's day- ignores or acknowledges Valentine's Day can be a very accurate predictor of the future state of your relationship. We may resent the commercialism of the holiday, we may sulk about it (giving it names like Single's Awareness Day), but we can't escape it in the dating world. Now Shanna, on to your story at hand and how we can lay a man trap before Valentine's Day!

You've provided a good summary and I'm sure you've left out the gushy stuff, but it sounds like you really like him... or could really like him. Most of our discussion will be in the analytical, left-brained camp, but it's helpful to remember to pay attention to those intuitions as well. Studies show that the decisions we make are 80% based on emotion. The 20% logic is generally used to make us feel good through justifying our decision after it's been made. So why this guy? What is it about him that he possesses that is so much more different than the others you have been dating? Have you really sat down and tried to isolate his qualities and what you like about him? We all have that "What if.." voice in our heads. It's a pillar of romanticism. The voice spurs us on to risk the unknown, ever since we were kids in elementary school passing notes to each other with "Do you like me?" 'yes or no' check marks.

Then there are the facts. From what you've described, it appears your previous encounters have only lasted a week or so and they were mostly initiated only because you bumped into each other. Of course you were dating someone else at one point and if he was aware, this could have added to his hesitancy. I would venture that timing may have something to do with it for him as well. There are many stories of happily married couples who knew each other for years without a definite click and over time they saw each other in a different light. Don't give up this lovely possibility. But definitely don't rule out the more probable possibility that this may be a case of "out of sight, out of mind" or convenient exchanges when you're both between relationships. You've had a conversation with him about not wanting to feel forced into doing something. I sense that he expressed a strong opinion or that there is more detail to this conversation. If this is the case, LISTEN to the hidden message. Both men and women use metaphors and generalizations because they DO want to keep options open and most DON'T want to hurt feelings. But if anyone uses heavy words similar to "forced" or "space", there is no clearer message that you need to walk away, and fast! If you're still unsure and don't want to live with regret, here's what you do:

Most guys are not idiots. Give him a once and for all, straight pitch right over the plate while letting him know you are available. As you correctly said, don't verbalize your intentions, but either get him to invite you on a date or you invite him somewhere. If he swings, keep it up until it would be obvious to any MAN, not WOMAN, that you are interested in dating him and then back off and let him take over the majority of the pursuit. We can help you later on that part if you need help clarifying what obvious is to a man:) If he balks after a few honest attempts, talking about it won't put you at any more loss than what you have now. Have a talk, trying to make it as non "business-like" as possible. If you begin dating again, Valentine's will help you clarify his intentions. If this doesn't work, bring up the next batter. I've lived in Virginia and there's plenty willing to play the game! Life is way too short to continue spending resources on someone who is unavailable. He may continue to send you texts, etc. even if he doesn't take the bait, but these will be symptoms of his commitment issues, not of his affection for you.
-DM