Fast-Forming Phone Friendship

I have met this one guy who I really want to meet in person to see if what we have on the phone is real, and, if it is, I want this one to be the last one. I want him to know I like him, but I want to keep things casual while we build up a relationship. I do tend to wear my heart on my sleeve, but for him I will try to keep it inside my shirt. Got any tips?

-- Gay

Kelly Says:

All you've done is talk to this guy on the telephone and you're already thinking about a lifelong partnership? That's worse than pigging out at the all-you-can-eat breakfast buffet and talking about what's for dinner at the same time. Or paying down $10 on your overextended line of credit and assuming you've now got cash to buy a hot new Vespa. You gots to slow down, Gay. Way down. Take things one step at a time. As in, try meeting the guy in person first before you decide you want to let him into your pants permanently. Spend the time to get to know him as a person, not just as an idea. If you let him know what your high-falutin' hopes are at this point, you're going to scare him away faster than you've already scared me.

Brent Says:

Have you already picked out your wedding dress, too, Gay? Slow down. Slow waaay down. The worst way to go into a relationship is with a specific end-goal in mind. It only puts undue pressure on everything that occurs between you. That leads to over-analyzing gestures, phrases, missed telephone calls, etc. And that leads to an ended relationship faster than you can say, "My ex-girlfriend was such a psycho." Why don't you try living in the moment? Enjoy spending time with him and park those nasty expectations. That way, if you have a bad date you can just shrug it off and blame the calamari instead of stressing about its impact on your invisible game plan. I can tell you from experience that if you don't, he'll smell desperation from a mile away and it will kill any chance of long-term happiness before you even get started.

Always a Friends, Never a Flame

It's been about a decade since my last sexual relationship. I get along well with women, have no problem talking to women, and am straight. It always seems, though, that there is someone who looks better than me, is better off financially, or is of a more preferred color (I'm white and I've had women tell me I'm the wrong color for them). I always get the fabled, "It's not you, it's me." I usually end up helping these women pick up the pieces after they get dumped, scammed, beaten, etc. Some tell me I'm going to make a woman very happy someday, then leave to find more of what they just left. This is not a localized phenomenon centered around five or six women, but a recurring theme no matter what I seem to do. My question is, What the hell am I doing wrong?

-- RCloak

Brent Says:

This is a two-part question. The first part of the answer is: stop being so fucking nice. No matter how much women will deny it, nice guys bore them to tears. They want some adventure and spice in their life and the guy whose shoulder they cry on is not the guy they want to end up with. He's safe. He's Melba toast. He's just too, nice. So instead of letting yourself get walked all over, next time they want you to hold them while they cry try telling them they got what they deserved for dating such an asshole and let them figure it out on their own. See they're using you for the male emotional support they need to feel better about themselves, but as soon as they do feel better, they'll be off to bang the first dickhead in a Camaro they can find.

In terms of why there is always someone, "Who looks better than me, is better off financially, or is of a more preferred color." Stop whining. That may sound harsh R, but that's what I see when I read that, and it's likely what the women around you are seeing to. See, dating is a confidence hunt. Women are looking for a man who is sure of himself and if you can't project that you're dead in the water. Do you think those ugly guys you see dating supermodels are sitting around saying, "There's always someone better looking than me?" Fuck that. They're going out and hitting on every hot chick they meet until one agrees to hop into the sack with them. And it works because they're confident. So snap out of it, stop feeling sorry for yourself and go get laid.

Kelly Says:

Repeat after me: "No more Mister Nice Guy." You need to inject yourself with a serious dose of confidence and put some work into portraying your sexy side. Sounds to me like the ladies see you as an über-sweet guy who's perfect for shoulder-crying and rebound-retaliation but who doesn't possess any of that bad-ass animalistic charisma that many women open their legs for. Maybe your appearance (wardrobe, hairstyle) needs a masculine makeover. Ask a good friend -- female, if possible -- to coach you on your style. Talk to them about your dilemma and ask them why they think you can't seem to hook up with anyone worthy. Tell them to be brutally honest with you, that having your ego crushed once by a caring friend is always better than being hurt by a lifetime of romantic disappointments. Although it sounds like you've been used and abused by some doozies this last decade, those past flings were right: You are going to make a woman very happy someday.