Dear Demi,

I’ve been best friends with this girl—let’s call her Karen—for almost 16 years now. We met in 7th grade homeroom and since then we’ve been super close. It’s the closest relationship I’ve ever had. We’ve both been through a lot of growing together over the years. Over that time, we have had a few drunken sex encounters. She’s the only girl I’ve known that I can say I truly love. But we’ve always stayed “just best friends.”
For the past five years I’ve been living out of state, but we stay in close contact via phone and flights back home. It’s been real hard. I miss her to death. And the more time I spend away from her, the more I think I should try and take our relationship to another level. But there is always that voice in my head saying, “Don’t do it, dude. It’ll ruin your friendship.” It’s crazy. Every girl I meet out here (SF) I always end up comparing to “Karen.” Which I know is not fair at all, but I can’t stop myself.
What do you think? Should I get over Karen, spend less time being close to her and try to find a new girl? Or make an attempt to ‘seal the deal’ with Karen?

Signed,
Just Wants To Be Loved

Hey JWTBL,

You poor sucker. This is a common deal. But though it happens all the time, it’s still tough and it doesn’t usually end well.
I know you feel compelled to confess your heart to “Karen” because you’re stuck in this frustrating limbo. But believe me when I tell you, JWTBL, “Karen” is in full knowledge of your feelings. Guys can be good liars and such, but they can’t for one minute fool a woman they’ve been so close to for so many years. No man hangs around a woman that long, that closely, who isn’t waiting for something more. Plus you’ve already fucked a couple of times and you STILL hang around all happy just to be near her. Men don’t do that, OK? Once you fuck, it’s either the next step or it’s lose-my-number time. She knows this, and since she knows and hasn’t given you the green light to go further, she most likely digs things the way they are. Show me a chick who doesn’t love the ego boost of some poor shmuck waiting for her to love him back and I’ll show you my high school gym teacher.
You’re what girls call a “nice guy,” and that sucks. Nice guys do tend to finish last in these situations— unless they can somehow switch roles with the girl they’re after. Right now she’s got all the power over you. She’s the gate keeper, so to speak. In order to get what you want, you’ve got to be on top. You gotta grow some hairy balls.
Here’s what you do. Tell her everything. Tell her on the phone. Tell her that you’re not looking for any yes or no answers or any decisions on her part. You just want her to know your feelings. Then don’t talk to her for awhile. If you always call her, let her call you a couple of times before you call her back. Have cheap rough sex (safely please) with some willing ladies and try not to think about this for a while. Put “Karen” a few pussies behind you. Believe me, she’ll feel it. Women can smell other women on men from across state lines, and it makes the man more attractive. You know when you hook up with someone and all of a sudden all these chicks from everywhere in your life start calling you, some of them coming on to you? It’s kind of the girl version of peeing on something to make it yours.
Let “Karen” chew on what you say and get a taste of life without you. Don’t be extra available to talk about your confession— she’ll just milk you for extra ego points that will only translate into her self assurance while going after other guys. Tell her what YOU want. Be firm and direct. Then leave her alone with it.
If it doesn’t turn out the way you want, move on and don’t look back. Lots of times the object of your affection will realize you were THE ONE once you become unavailable to them emotionally. Whatever you do, don’t fall for it. You’ll be in a worse position than you’re in now. Not only will you still be her nice guy, you’ll also be a chump.