Dear V,
I’ve recently formed feelings for a guy who is in my social group of friends. I love the dynamic of the group and after two horrible relationships I’m terrified of starting a new relationship, and I definitely don’t want to ruin the stability within my group. We’ve definitely flirted before, but what’s the best way to ask him out without completely risking our friendship?
Undercover lover
Dear Potential Hollywood Script,
Yes, the old “I really like my friend but I don’t want to ruin our friendship” routine. Everybody likes to ask “What’s the best way to ask someone out?” and the truth is, there’s only one way to ask someone out, and that’s just to do it. You may have been expecting me to recommended you isolate the two of you in a forest meadow, flowers in full bloom, chipmunks and rabbits waltzing hand in hand in a circle around you while you read Margaret Atwood poems to him as he melts away and becomes one with the earth below him. This has never, EVER happened in history, so your best bet is simply to ask him if he wants to hang out with you alone. I once asked a girl who was a really good friend of mine out and got rejected. Today, we are still great friends, and my feelings for her have subsided to just friendship.
Moral of that story (other than me being a chump) is that “risking friendship” in most cases is more paranoia than reality. Yes, it does make it awkward for maybe a month, but ultimately, if you’re really friends, you’ll talk it out with each other and realize that it’s better to just be friends. If they share the same feelings for you, then taking that step into the unknown may have produced a result you never would’ve had if you didn’t have the courage to say what you felt. Sometimes you have to go through with something even if you think it’s a bad idea, if nothing else, to give yourself some closure.
If you want to start slow, you can do things together as “friends” to get a feel for each other. If you take that approach, don’t recommend anything too romantic, or you’ll tip him off, and you send him mixed messages he’ll be confused and uncomfortable. For instance, don’t go to the movies as “friends” and watch a romance movie (even romantic comedy is stretching it). Watch something like “Batman,” or “Transformers.” While these movies do have romantic subplots, there’s enough action to put his mind at ease.
If you don’t want to go slow, you could just tell him how you feel right away, but only do this if you feel like you have pretty good chance. Which route you take is up to you, but if you keep him waiting too long, someone else might come by and snatch him up.
Ball’s in your court, just try to do more with it than Chris Dudley did,
V
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