Tom, 25

You look a little intimidating, standing there shirtless with that large piece of wood. What’s the best way to hit on a surfer on the beach?
Talk to me. I’ll make it happen if I see that someone wants to hang out.

I can’t swim, or even hold my breath underwater. I’m also not very athletic and not very willing to try. Are we completely incompatible?
Honestly, a lot of dudes who surf prefer dating girls that don’t surf because if they do, we have to take them surfing all the time. When you have to go to spots with smaller waves, it ends up being kind of a pain in the ass. 

Are you suggesting that boys are better surfers than girls?
I’m saying, in my experience, having girlfriends that surfed made it... a lot more of a chore to go surfing.

Does surfing get you laid more than the average dude?
Definitely. I’m on the beach all day.

You’ve also got all these foreign girls coming in for vacation.
Yeah, exactly. Are you going to like…is this like one of those Candid Camera-type things?

Don’t worry, we’re all the way in Hawaii — no one will ever find you. My girlfriend asked me if she looked fat in what she was wearing. Because she recently has gained some weight, I used the opportunity to gently tell her. Bad idea. Not only is she still angry, but I seem to have seriously affected her confidence, to the point where she doesn’t seem to be enjoying sex lately. How can I reassure her?
Be affectionate, and tell her you love her.

Have you ever made a mistake like that?
No, I’m not that stupid.

I’m dating a bunch of different guys right now, though none of them are very serious. Recently, one guy hinted that he knew I was playing the field. Does he want to be exclusive? Or is he displaying weird signs of jealousy? Do I need to be honest with everyone I’m dating that I am a serial-dater?
At that point, yeah, you’re kind of messing around. But I wouldn’t tell anyone. If someone calls you out on it, though, you should tell them.

My girlfriend is extremely loud in bed. I enjoy it, but think she could turn down the volume a little bit. What’s a good way to approach the situation so that she doesn’t get offended?
I think it’s weird when chicks do that. I guess I’m a pretty outgoing person, but stuff like that is kind of like... come on. It’s not exactly a turn-off but it’s like, “Oh shit, who am I dealing with?”

Are you quiet in bed, Tom?
I wouldn’t say I’m quiet, but I’m not yelling and screaming.

What’s the nicest way to reject someone you’re not interested in?
If the person is up front, just say, “I just don’t have those feelings for you” or something like that.

Something cliché and awful?
It’s better than telling someone they’re ugly. That’s pretty brutal.