Meet our friend Tom. He’s a married guy with tons of relationship experience, and a skilled advice giver who’s here to answer all your pressing sex, dating and relationship questions. Have a query for Tom? Email it to email@example.com and we’ll make sure he gets it! All questions will be posted anonymously, unless otherwise requested. First up…
“I’ve been spending a lot of time with one of my guy friends. I’m starting to have feelings for him, and suspect he might have feelings for me too. How do I know for sure that he’s feeling something more than friendship and how do I go about bringing up the subject without being too weird?”
My first instinct was: “Ask him out, you chicken.” But that’s a mistake. When a man successfully asks a girl out, it’s the greatest he ever feels. The birth of his first child will be a huge disappointment in comparison. Like “Matrix: Reloaded.” Success with women is a male emotional speedball. Imagine how good River Phoenix felt right before the end. It feels THAT good. So you cannot deny him this. Plus, his emotional overdose is fuel for the rest of the relationship. Let him ride the dragon and he’ll chase it all the way up the aisle.
But right now, he’s being a wuss, because all men hate rejection. Make it easy. Don’t bring up the subject at all. Get a BACK CHANNEL. Invite a close female friend over for a low-stakes hangout. Ask her to spell it out to him when you go to the bathroom: “She has a huge crush on you. Just ask her out. Or better yet, kiss her then ask her out.”
Then give it a week.
If he asks you out? Fantastic. You’re at the races.
If he doesn’t? Here’s the hard part: it’s the end. You can’t hang out with him any more. Period. Be polite about it. You don’t have to say: “I can’t hang out because I like you too much.” But you must always have other plans.
This is why. He has one of two problems.
Problem One: He is so paralyzed with fear of rejection that he is never going to ask you out. A person suffering from Problem One is really fragile and will require years of remedial sex coaching (by you). If asking girls out is impossible for him, he’ll never know the importance of yanking your hair back while you fuck in the laundry room at a stranger’s house party. That’s a black hole project.
Or, Problem Two: He has such a deep well of insecurity that he needs to keep girls dangling on a string that he has no intention of dating. We’ve all done it. He may not even be fully aware he’s doing it. It doesn’t make him a bad person. But if you keeping hanging out, hoping today’s the day he whips out the poetry and baby names, you’re enabling some bullshit.
So don’t be sucker for that. Give him seven days, then get on day eight, hit OK Cupid. Don’t talk back, just do it. I’m not telling you to just go fool around with someone. (Although as a man speaking for my people, that’s fine too). Just find a nice guy and go out for a nice dinner. I’ll even recommend one: comedian Joe Pera. He’s amazing. He’s sweet, funny, and do you know what his OK Cupid handle is? NiceDinnerGuy. You can’t go wrong with that. Look him up, or someone similar, and get out there, because your life is too important to be moping after a guy who isn’t yet emotionally capable of taking risks.
So, to sum up: use a back channel. If he takes the hint, it’s go time. If he doesn’t, get a nice guy on the Internet to by you dinner. We call that a win-win.