Q I'm a 24-year-old guy with what I think is a pretty good lot in life. I've got a good job and fun friends and (mostly) good family. But the one thing I desperately want to change is the relationship with my best female friend -- I want to date her. I've been secretly in love with her for about a year now. We're super-close already. We talk and text every day, and we're each other's fallback dates when we have nothing else going on. We've slept in the same bed before, after too many drinks where one person couldn't drive home, and I've been too afraid to make a move. Now, my feelings are even stronger. So, what do I say? And what should I do, if, God help me, she doesn't feel the same way I do?
-- Agonized
AYou want to be her boyfriend? Then stop being her girlfriend. Start by becoming unavailable. Fill your schedule with new friends -- including other girls -- and activities, and resign your status as her fallback date. You've got to get her to see you as a guy, a sexual being, not just as someone she can call for a night of Netflix and foot massages.
While you're at it, jazz up your look: Get a haircut, some new duds, replace those tired old glasses with contacts, hit the gym more often. (Physical self-improvement is the little blue pill of self-confidence, after all.) Be busy -- and, truly be busy, don't just say you are -- for at least three weeks, and then call her up and say: "Hey, we haven't seen each other for a while. I want to take you out." Then, organize a real date, pick her up and pick up the tab. At some point in the night, either 1) ask her if she's ever thought about the two of you dating; or 2) just kiss her already.
At best, you'll have an amazing new girlfriend; at the worst, you might lose a friend. Either way, you won't have the agony of not knowing anymore.
Q Can you please help me out with how I should approach girls at the bar? My buddies and I enjoy going out for beers on the weekend and to watch games and stuff, and they have no problem just chatting up women. I'm more shy, and it's not as easy for me. I don't know whether I should walk up to a girl who's by herself or if I should wait until one of my friends makes a move on one of her friends or what. Or if I should ask for her number or e-mail, or how many days I should wait to call. All I know is I'm tired of being the one who always goes home alone at night.
-- Baffled Barfly
AFirst of all, take a deeeeeep breath, and try not to get yourself worked up into any more of a tizzy than you already are. The key to making a good first impression on women is calmness, which begets confidence, which begets lots of other bonuses in life -- not just the ability to chat up the hottie in the corner.
You're shy -- that's a trait plenty of women find endearing. So use it to your advantage. While your bolder buddies ham it up with the Barbie dolls and rounds of Irish car bombs, strike up a conversation with that cute brunette who, like you, is probably just taking it all in from the periphery. Don't worry about throwing out slick lines; a simple, "Hi, I'm ____" with a warm smile does just the trick.
From there, see how the conversation goes. After a few minutes, if things are going well (i.e., she hasn't dashed off to the bathroom) and you take a shine to her, ask for her number (or business card; never an e-mail address). If she gives it to you, great; if not, don't fret. Just smile and say: "No worries. Nice talking to you."
Whatever happens, eventually walk away. If she's shot you down, it takes the pressure off her to keep chatting with you; if you've got her number, it establishes you as a confident guy and leaves her wanting more. Call her within a day or two (don't text), and, for God's sake, don't ask for her phone number if you don't want to see her again. It's just fine to have a conversation for conversation's sake at a bar; girls don't assume every guy who talks to them wants to get in their pants.
Speaking of which: I promise your buddies aren't getting laid every time they bring a girl home. Stop comparing yourself to them and get comfortable talking to women as equals, not just as conquests to bag after a night of barhopping.