Ladies! We brought your latest post-dating quandaries to a guy who is quite the triple threat. One part life coach, one part sports nut, and one part decoder of ambiguous text messages, this week’s dah Guy tackles your questions about meeting men, making the first move and revealing your “sex number” with a calm wisdom that will leave you feeling way more zen about your love life than you did five minutes ago.

Now, let’s get those questions answered…

To submit your questions for next week’s guy, email us at  with “Ask a dah Guy” in the subject line!

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Question #1: Here’s the nitty gritty: until last month, I’d been living with my then-boyfriend for two years. We were in love, and then we weren’t. We’re broken up now. I’ll spare you the nasty details.

Now I’m done moping around my (new) apartment and want to get back out there and rebuild my dah or find someone new or whatever makes sense. I have a very active social and professional life. Everywhere I go, though, I feel like I just meet more girls! Or cool guys with girlfriends. I’d hoped to meet guys through friends, but almost all of my friends are in relationships and seem to only be spending time with other couples. Or they say they don’t know anyone “good enough” for me. Ugh.

So – where are the (nice, fun, cute, mature) single guys these days, and how do I find them? And please don’t say online dating. Not my thing.

Firstly, I want to quote Don Draper: “I’ve started over a lot in life.  This is the worst part.”

Congratulations on pulling the trigger and removing yourself from a pointless and complacent situation.  Basically, you just went from an incorrectly filled-out form to a blank sheet of paper, and that truly is the worst part – the empty lines.  The crippling pressure of potential can often lead us to grasp at anything in arm’s length, in order to fill the space left by something that used to be. But it’s important to remember the point of potential: opportunity.  Yes, choices will have to be made and mistakes are inevitable, but this is an opportunity that you might never have again.

You say you are active in your social and professional life, but what about your life?  Not going out for drinks, or working the room at a networking event. Are you doing things that fulfill you? Things that stir your soul?  Are you doing shit that you love?  To sound like a total ass, I meet people everywhere I go, and I am not particularly above average in any way worth noting – other than one.  I know the shit out of myself.  I form opinions easily, make decisions swiftly, and put myself in places and around people that are receptive to that individuality.  I make mistakes, and fail at things constantly, but it’s all part of the opportunity I have been granted to live this life.

When you are on the pursuit of self, people will be drawn to you, and you will see who is worth having around, who makes you better, who pushes you, who makes you laugh.  Don’t worry if the guys you’re meeting have girlfriends, and don’t fret over asking your friends to set you up. Just talk to people. Don’t put yourself out there just because you are looking to fill up spaces in a prefabricated form.  Make your own form and let the answers come naturally.  Be a person first.  Go to places you want to go to.  Hang out with friends who make you better, even if they are guys with girlfriends.  If you can learn from them, don’t see them as a waste of time.  Enjoy the opportunity you have to be you, and screw worrying about checklists.

There are single guys all over the place, but the truth is, after a certain age, many people just pair off because they think they have no other choice.  The people that don’t, that are looking for something real, need to see you for who you are.  They need to know you are a strong and confident individual.  I know this time is hard, but you’re going to go to the places you want to go to, do the things you want to do, and meet the dudes you need to.  Cheers to you, my friend.

Question #2: A couple months ago, I joined a basketball league in my city (I know, group-non-date!). It’s been really fun, and I think the captain of our team is really cute. 

A couple weeks back, he texted me about a time change in our game, and the conversation turned casual and jokey. Ever since then, we’ve been texting pretty regularly – once a day usually, or at least a short convo every other day – and I noticed a flirtier vibe at our games since then. BUT, he hasn’t asked me out or anything. Just casual texting and gameday flirting.

My question: how assertive can I be here? Can I ask him to hang out one-on-one, or should I wait for him to make that move? Should I assume that he’s just shy, or that he’s just not that into me?

This is an easy one.  You should definitely make the move.  If you feel like you guys have a connection and want to ask him out, do it.  He will most likely appreciate you for taking the initiative, and if he doesn’t, he probably isn’t your speed anyhow.

There is a good amount of pressure on guys to say the right things, make all the moves, be omnisciently aware and without doubt in these situations – and sometimes that pressure can cause a block.  The worst thing that could happen is that he isn’t into you like that and he says no.  You walk away a little embarrassed, but that’s only your ego, and the ego bounces back pretty fast.

Question #3: I’ve gone out with a new guy four times, and I’m into him. He’s hot and funny and the sex is good and he likes weird tribal music as much as I do. 

But – the last two times we’ve hung out, he’s asked me about “my sex number.” WTF? Does anyone still care about that? I find it offensive and annoying. And, to be completely honest, I like him and am a little nervous that it’s going to change something if it’s higher than he’s expecting. I mean, I’m 28…

Should I tell him my number and risk things getting weird? Or avoid the question and risk things getting weird in a different way? And why would a guy even care about that anymore??

A relationship built upon a mutual love of weird tribal music is a rarity and something to cherish, but I agree with you about the sentiments toward the “sex number” question.  In my opinion, that is a completely pointless stat (for lack of a better term), and like most stats, it isn’t a true representation of the player’s ability, talent, and composure in game time.  The only reason someone would care about that is insecurity, or worse, he is eager to tell you his number, as if that is some accomplishment.

If he really wants to know, tell him, because if it is insecurity, you withholding the information will only increase that.  But when you tell him, ask him why he wants to know.  Try to get to the core of why he cares about it.  That should tell you a lot more about who this guy really is.  If he’s into you, I can’t imagine that would actually have an effect.  If it does, you can chalk it up to immaturity.

Thanks to Nagarjun for this adorable image!