Q. Is a FWB relationship ever ideal to a woman in the long term? Or do you hope for a serious relationship/commitment after repeatedly hooking up with a guy?

A. I think a friends-with-benefits relationship has an expiration date for everyone, not just ladies. Eventually it's not really enough, or one person starts to blur the lines between the friends and the benefits part. I don't think all girls are incapable of it just because they are hoping they might wear you down. Sometimes they just realize that while they are spending time hooking up with you and hanging out with you, they aren't really available for meeting someone else. I have a hunch that dudes can sense when a girl isn't really single even if we say we are.

Q. So I'm home from freshmen year of college (it's an all-guys college) and I want to make plans with my ex-girl-friend of eight months from high school who I haven't seen in almost four years (I switched schools). We talked a lot over Skype my first semester at college and it's obvious that we both want to see each other again. Now that we're both home I can never get her to commit to plans for lunch or to go see a movie. Her friends say I should just show up at her house one day because she’s "being shy." I know she wants to see me but I'm not sure if surprising her is a good idea. What should I do to get her to commit to a date with me?

A. Definitely don’t just show up at her house. Surprises aren’t always received that well.

 

 

Q. I was talking to a girl at college a little while ago and she bought me a pretty expensive birthday gift. I ended up cutting things off with her but we are still friends. Her birthday is coming up. Should I get her a gift? We never actually dated but we are still pretty good friends. I don't want to feel like a douche because her gift was pretty nice.

 

A. No. Send her a hilarious http://www.someecards.com/ someecard, and buy her some birthday shots. If she got you a gift while you guys were still dating and now you’re not, there’s no reason to get her something. She wouldn’t be expecting it and it also might send the wrong message. You should definitely acknowledge her birthday, hang out, do something fun, but keep it squarely in the friend zone.

 

 

 

Q. How do I show a girl that I am confident?

 

A. First and foremost, "confident" does not necessarily mean the loudest and most attention-seeking dude in the room. I often find theopposite to be true; those dudes end up being pretty insecure and are generally over compensating. Fun fact about yours truly: If there is one trait that can be traced through every guy I’ve ever had more than a passing interest in, it’s confidence. All of them had the ability to strike up entertaining and interesting conversation. Most girls don’t expect a guy they don’t know well to be able to have a conversation with them for more than a minute or two. If you want to show her you’re confident, talk to her. Like a regular person. Don’t bust out stupid one-liners, don’t brag about how many games of beirut you’ve won, or how big your bonus was at work this year. Just. Be. Yourself. If you’re good with doing that, she’ll pick up on it.

 

 

 

Q. Is it f*cked to tell a girl she’s a terrible kisser if you have the intention to give her pointers?

 

A. I suggest treading very lightly with that kind of comment. Try to say it as constructively and gently as possible. AKA, don’t tell her she’s a terrible kisser, tell her you like it when she kisses you a certain way (aka the way you want to be kissed) and see how that goes. Giving pointers isn’t a bad idea, just couch them gently. Also, reward for good behavior. Like say how much you like making out with her, when she does it properly. And hope that she’ll catch on! Just be nice. Or else you’ll end up with no one to kiss.

 

 

 

Q. What languages do you know?

 

A. French, though not fluently. And about cinco words in Spanish.

 

 

 

Q. Will you draw me a picture of a Unicorn with a badass hot chick riding it? Maybe make it so the badass hot chick and the Unicorn are about to fight a dragon.

 

A. This might be one of my favorite questions ever received. If I had any artistic abilities at all, I would certainly acquiesce this request. Alas, I do not. But this guy does. Send your request over to him and see if he'll draw it.

 

 

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