So, this is a classic case of "I have a friend I like like that and I don't know what to do about it"! This guy and I have been hanging out since about September of '06; we met at a friendly gathering, and had a lot in common right away: similar interests, personalities, etc. and we got along well. We hang out frequently & talk or text almost daily; we exchanged Christmas gifts, I got him a birthday present, etc. I took him to the doctor & took care of him when he was sick. He helped me move & has attended some social events with me, yada yada, yada.
We've never officially been on a date; we've gone to the movies together & dinner, but we usually each pay our own way or whomever has the cash at the time buys. We're planning a trip together this summer; we'll be in his hometown, so he's staying with family & I think I'll be staying where the event is being held. Thing about it is, I really like this guy. I go back and forth on how he may or may not feel about me CONSTANTLY, and the minute I think all is platonic and I get comfortable with that, he does or says something (surprises me with a gift, makes flirtatious comments, etc) that makes me think otherwise.
Neither of us is dating anyone, and we haven't since we started hanging out. He gets defensive when I start talking about other guys, but then occasionally he'll bring up other girls, too. I don't know if I should jump in at let him know what's on my mind, or be content with the friendship, which I'd HATE to lose. I think if I do tell him, I might mention it on our trip. HELP! -- Platonic Pam
To see DEARSUGAR's answer
Dear Platonic Pam --
Wow. This really sounds like a wonderful friendship; it also sounds like really solid ground for a romantic relationship. The thing is about honest-to-god friendships, they're not as fragile as we imagine, Pam. I've been on both sides of this fence -- I'm sure many of our readers have, too -- and where there was genuine affection and friendship, we always made it through the initial awkwardness. If you knew for a fact you wouldn't lose his friendship, what would you do? I know this requires real emotional risk on a few levels, but from what you've described, it sounds like a risk worth taking.
I like the direct approach, but that's the kind of girl I am. What about waiting until after the trip? (In a perfect world, without a booked vacation, I'd say do it now. You might really think about that anyway, Pam.) Either way, the fellas seem to need to be doing something, some activity, during these kinds of conversations, so broach the topic at a casual dinner or on a walk. Be honest. I don't think playing it cool ever really works, especially if someone knows you well! Tell him he's one of your favorite people and that you consider him a brilliant friend. Tell him you feel nervous bringing it up (if you are), because more than anything else you want him to help you move again someday, but you were wondering if dating each other might be an interesting thing to do next?
Make sure he knows you're serious, Pam, and not just playing around. And make sure he knows you're perfectly willing and perfectly able to remain his friend if that's what he thinks is best. Sometimes life asks us to pull back the curtain and reveal ourselves. Since you asked, I say be brave, be yourself, and let the chips fall. I get from your note that you're pretty much there, Pam, that you'd like to know what else might be possible. It will feel terrifying. It will also feel like an enormous relief, no matter what. Courage, courage, courage, cowboy; I saw this written on a wildly whimsical painting & I say it to myself quite a lot ever since. Now it can be your mantra, too. Promise us you'll follow-up here? Please. Ladies, what do you think?