Dear Wanda and Wayne,
I love your columns and I wonder if you have some advice for me. One of my best friends is visiting soon and for the first time we're both single and I'm thinking about making a romantic move on her. We've been through a lot of life's ups and downs together over the years and feel like best friends and family. But there's also always been a romantic kind of chemistry between us too. But like I said, the timing has never been right and we've both seemed to value our friendship more than a romantic opportunity. We've even shared beds and tents together on trips and vacations but have never even kissed.
She's spending next week with me and we're going to be hanging out almost the whole time. Right now I can't stop thinking about her and about kissing her and telling her what she means to me, but I am also super anxious about having it all blow up in my face, or at the very least get really awkward. I'd hate to lose her or even mess things up -- we get along so well. And I'm confused, honestly -- there are times when I think she could be my wife or she could be my best man.
Any advice before she arrives? Thanks.
-- Old Friend
Wayne says: Isn't that exactly what we're all looking for? A partner, a best friend, a confidant, someone we have fun with and are madly attracted to? And she's right there in front of you, man!
I respect your integrity in not making moves on her when she and/or you are in relationships with other folks. And I appreciate your hesitancy to jeopardize a relationship with your bestie -- why mess up a good thing? Here's why: She could be THE ONE! Perfect fits don't come along very often, if at all. Ask the hundreds of lonely folks who write us every year or the millions trolling around online dating sites at this very moment.
So go for it, buddy. Could be the best move you've made in your life. Or it could be a bust. That's life and it's better than wondering for the rest of your life. If your move blows up in your face and you two are truly the best friends you claim you are, you'll both be able to shake off the awkwardness and move on fairly quickly and unharmed. And maybe even laugh about it when she gives her best man speech. Right, Wanda?
Wanda says: I'm all for seizing the moment. If you make a move and all goes well, just think, won't this make for a romantic story at the engagement party? "All those years, the love of my life was standing right in front of me." I can just hear the champagne glasses clinking now -- and hear the pinging symphony of smart phones as winsome singles text their besties: "Miss you, thinking of you..." Because it sure would be convenient and awesome if the one we were looking for was right there all along. In your case, maybe your female friend is your Mrs. Right. With the stars at last aligned, you can confess your affection and ideally, and she may readily reciprocate. It's an intoxicating fantasy, a Hollywood ending to your own "When Harry Met Sally" storyline.
But it may not end that way. Say you lay it out on the table, admit your emotional attachment to her, tell her you've always been attracted to her -- and she's shocked. Maybe she doesn't feel the same way. Even if she does, maybe she doesn't want the friendship to change. Wayne suggests that in the face of failure, you could both laugh it off and go back to normal. Easier said than done. The moment you try to turn a friend into a romantic partner, things have changed and can never be exactly the same again. If you pursue her, you are risking ruining or at the very least altering what sounds like a special friendship.
I'm not trying to scare you out of going for it. It sounds like you've thought this out and care deeply for this woman. Just proceed with caution. Feel out the situation before you leap. Treat her to a fancy dinner her first night in town. Talk about where you're at in life and feel her out, too. Flirt with her. Compliment her. Make long lingering eye contact. You'll know in your gut whether she's feeling the vibe or is feeling freaked out. Then move forward from there. We certainly hope it works out for you. Everyone loves a Hollywood ending.
•Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at firstname.lastname@example.org.