Jerome, 27
What’s the best way to hit on a surfer on the beach? “You have huge muscles and a big piece of wood.” Wait, are surfboards made of wood?
Tourist point of view or local?
Let’s do both. Tourist first.
Start by having an opener, like, “Hey, can you tell me where to go? What’s happening tonight?” If you’re a local, ask if they have any extra wax you can use. It’s a little white lie, but in the end it’s all about breaking the ice.
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?
That’s more of a reason to get you on a surfboard and take a risk. That builds trust. Trust is a good way of establishing friendship, and if you’re in danger of drowning, you’re in good hands.
How would you coerce me into surfing lessons?
I’d show you some techniques on the sand without even getting in the water.
That sounds so sensual.
Then we could go a little bit out within standing distance and give it a try.
How is surfing like sex?
They’re both very physical and emotional; you get into the moment. You lose track of the time, and at the end of the day, you get tired and want to sleep, or hungry and want to eat.
I’ve been dating a guy for a few months, and we're really happy. The other day though, he told me he loved me. I froze, because it was so unexpected, and then said, “Thank you.” After I thought about it, though, I realized I do love him. How can I repair the damage of my surprise answer?
I’d say "love" is a little bit overrated: it’s used so often that “Hello” practically has more substance behind it. If you take away the titles, the labels, having that trust, that friendship between you, it doesn’t matter whether you say it or not. I prefer not to say it at all, because then the one time I say it, it actually means a lot. So if you want to mend this situation, sit down and talk. One of the weirdest things nowadays is how everyone’s texting. Everyone is antisocial. Technology is great, but people don’t know how to look each other in the eyes and talk.
My girlfriend asked me if she looked fat in what she was wearing. She actually has gained some weight recently, and so 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?
As kids you’re always taught to lie. Your dad tells you that when Mom asks you, “Hey, how do I look?” you say she looks all right even if she doesn’t. That little white lie will sometimes save you the drama, the headaches: words can do a lot of damage. But you can also suggest little things to help her look and feel better. Work out with her. Go to the gym together. Be a friend that way to her, be active.
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?
Well, it depends on the guy. You would have to take him to a bar and see how he reacts when other people say “Hello” to you. It’s like acting, playing out a scene. Body language can teach you a lot about a person whether he is jealous or not. In women's eyes, jealousy can be a good thing — a reassurance — but but at the end of the day, you don’t want a stage-five clinger.
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.
David, 30
You look scary: shirtless, surfboard, tattoos. Oh my. What’s the best way to hit on a surfer on the beach?
You know what? You just have to talk, you never know.
I can’t swim, or even hold my breath under water. I’m also not very athletic and not very willing to try. Are we completely incompatible?
No! It depends on other areas too, if you know what I mean, and what you’re looking for.
So you’re not looking for someone with a similar lifestyle?
You never know who you’re going to click with. I’ve been with all kinds of women.
How would you coerce me into surfing lessons?
I’d probably take you tandem — two people, one board — and help you all the way through it. When you feel comfortable enough, then you could probably take a lesson.
Would you make me wear a life vest? Would that be a big turn-off?
No, it wouldn’t. If you were by yourself, about to catch a wave, I might make you wear a life vest.
When I was little, I was sure that my uncle’s Sex Wax was something dirty. Do you ever use toys in the bedroom?
I am the toy.
Batteries included?
I’m an Energizer bunny.
How is surfing like sex?
[Whistles] Well… you do get a mean rush from surfing. There’s a mean rush from sex too, but a different kind.
Does being a surfer in Hawaii get you laid more than the average dude?
I wouldn’t say so. I do meet a lot of people, but I don’t sleep with a lot of people. If I see someone I like, I don’t just jump in bed with them. If you get to know somebody, it's more enjoyable.
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?
Not unless he comes straight out and asks. Just tell him you’re dating a bunch of guys casually: it doesn’t mean you’re sleeping with all of them.
Oh. I thought that was implied when I said “dating.”
Oh.
What’s the nicest way to reject someone you’re not interested in?
Let them go in for a kiss, and then make it the worst one of their life. Don’t move your tongue, just lay it in their mouth. Then they’ll reject you, and you can begin a happy platonic relationship.