A few weeks ago I recognized a guy sitting by himself at the bar who is kind of a local celebrity.  I was a few drinks in, so I went over and said “hey aren’t you____?”  He invited me to sit down and we talked for hours, he bought me a drink, and it was a lot of fun.  I don’t really ever deliberately flirt with anyone, and I didn’t think I was flirting with him very much, so I was surprised when he walked me home at the end of the night and he went in for a kiss. Cool!  I ran into him a week later and the same thing happened again (super chill, great conversation) except later that night he took me to a place where he’s a regular, and I met some of his acquaintances/friends.  So after another good night I texted him that I wanted to see him again.  He agreed enthusiastically, and we found a day that we’re both free.  He’s also 10-15 years older than me.

Now things get hairy. I heard a few days ago that he’s not single.  Hmm…  A little internet hunting (I know this is really stupid/weird and I shouldn’t do it, for my own sanity) and I find he’s claiming to be single, but there are definitely a lot of fishy things that lead me to believe he could have a (younger) wife or girlfriend-but he doesn’t acknowledge it publicly because of his popularity.  I think it would be fun to see him again, but I don’t want to look like one of Tiger Wood’s special friends.  How do I figure this out without seeming mad paranoid/insecure?

There’s nothing to figure out. You’re not gonna marry this guy. You’re not even gonna make girlfriend status. You’re gonna see him a few times, earn your starfucking merit badge, and then move on.

That’s cool. Nothing wrong with having some fun. Just don’t kid yourself into thinking that you’re signing up for any kind of relationship.

He’s got age, a little celebrity, and a reputation that obviously precedes him. Single or not, this guy is a walking red flag collection. You are not the only girl he’ll be bending over hotel room furniture, and if you can’t handle that, it’s probably best you don’t go all googly eyed.

What’s the best approach to get my wife to lose weight? I’ve done all the obvious tactics, such as offering to work out together, buying a gym club membership, suggesting she try a personal trainer. And I’ve done this is as low-key manner as possible, as casually as possible and as nicely as possible because I like her and because I know this whole thing can backfire. Now, she knows she’s overweight, too, and she’s not happy about it, either. I should say, too, I’m not looking for some kind of gristly Rene Zellwiger silhouette, just to have my wife be within 20 pounds or so of when I met her. So, that’s the surface stuff. The subtext is more gnarly, because, frankly, I don’t like having sex with a seriously overweight woman. My pride is offended, and maybe that’s trivial to other people, but not to me. It counts. But I honestly want to be positive about this because I’d like to get off on having sex with her and hang with her without feeling like yet another loser dude stuck with a hefty chick. I do work out, by the way, and I am within the BMI for my height, but not, you know, Ryan Reynolds buff. So you with the sore abs, what should I do?

Grossed out by sex with your fat wife? Sucks to be you, bro.

For the record, you’re a bit of a superficial douchebag. Everything you wrote about is the surface stuff, and you don’t have the slightest clue how gnarly the subtext really is. That’s okay, though. For the sake of your wife’s health, I’ll throw you a bone.

Let me break you two down quick and dirty. College sweethearts, both former athletes. You got married after graduation. You both wanted to wait to have kids, but she ended up accidentally pregnant within a year or so. Over the course of nine months she ballooned a solid eighty pounds, but after having the baby, somehow the weight just never came off.

It’s scary how I know this shit, right? Wait, it gets worse.

Your wife was in a sorority, and somewhere there’s a box or a photo album with a formal party pic from the Bush administration with you in a tux and her in a gown both grinning like idiots. Go find that picture. Seriously, go get it right now.

Are you looking at it? Good. See how hot your wife looked back then? Yeah well, guess what? She puked her fucking guts out about an hour before that picture was taken. Betcha didn’t know that.

That’s right. Your wife has been struggling with eating disorders her whole life, and this is probably the first moment it has ever occurred to you. Good times.

So, what does this all mean for you? Well, now that she’s married and let herself go, it’s gonna take a lot more than subtle hints and low-key gym memberships to get her back down to crazy weight. You’re not just battling the pounds she added during pregnancy. You’re battling years of self loathing and secret shame.

Obviously, she needs to get her ass to the gym, but beyond that I’d start with couples therapy. No joke. You two have a lot to talk about, and quite frankly, you’re a bit too dense to handle this on your own.

Trust me, you want to be in a safe place before you tell your wife that she’s too fat to fuck, and when the dam finally breaks on her inner turmoil, you’ll be thanking me that there was a professional in the room.

Good luck.

I have a long distance friend who I’m currently fucking. This past weekend, I screwed a different guy, and don’t know what to do, they’re both continuing to talk to me. When did guys actually start wanting to talk to the girls they’re casually fucking?

Right around the time girls realized it was perfectly acceptable to be fucking more than one guy at a time.

Relax, kiddo. You can keep them both, especially if one is casual and the other is a long distance friend. Neither of those come with expectations of monogamy, and until the day that things get more serious with either one, you don’t need to worry about anything other than having fun.

How can you tell a dear close friend that your not interested in listening their man drama without sounding like total cunt?

Look her in the eye and say, “Sweetheart, I love you, but we’re not going to talk about that right now.”

Be firm and polite, then promptly change the subject. She’s the one bringing bad vibes, and you’re just trying to keep the room positive.

If you come at her from a happy place, you’ll never sound like a cunt.

That’s where I’d have to disagree with you. I’m not a control freak, although I am jealous that he has those picture left in his phone. I came to you for advice, and you didn’t give me much of anything.

Yes, I did. I told you to slow your roll.

In other words, be cool and chill the fuck out. You don’t have any right to tell your boyfriend to delete pictures unless you’re in them, which means you’d be asking for a favor out of jealousy to get the exes out of his phone.

It’s not fucking worth it. Just trust me on this, okay? You gain absolutely nothing by having those pics deleted. In fact, you come off looking weak and insecure.

Sure, I could give you a detailed lesson in how to manipulate him into deleting the pics with a smile, but you aren’t paying me for this shit, and even if you were, I’d still tell you to back the fuck off for your own good.

There were girls before you. There will be girls after you.

Learn to deal with it like an adult.

My boyfriend has pictures of his ex-wife and ex-girlfriend still on his phone. He’s explained the situation that he hardly talks to either of them anymore, although he was involved very deeply and completely in these former relationships. The pictures bother me (example: his ex-wife in a sexy maid halloween outfit; his ex-girlfriend making that goddamn kissy face in a recent picture she sent him). Without seeming like a jealous control freak (which I am not), how do I get him to remove the pictures?

Um, you are a jealous control freak. You’re just not any good at it.

Not only are you in denial about your jealousy, but you lack the basic manipulation skills to convince a boy to delete pictures from his phone. Pathetic.

Your best bet is to slow your roll and hope you wake up cool tomorrow.

Good luck.