Dating Advice From . . . Sailors

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Todd, 22

What’s the best way to get into a sailor’s pants?

Rum. Rum is the sailor’s drink of choice. Rum is my one-word answer.

The guy I’m seeing wants to take me sailing on a date. What should I know before I go?

If he’s a competitive sailor, there’s a good chance he’ll yell at you.

Things got crazy one night and I slept with a coworker. What can I do to avoid rumors or awkwardness at the office?

I don’t believe in awkwardness. I think everything that’s awkward is awkward because it’s funny and that’s sort of how I roll. If you embrace the fact that it’s funny, it’s no longer awkward. But if you do something like with sleep with a coworker, I would say take the power position first. In those kinds of situations, there’s always the bad guy and the good guy, the innocent party and the guilty party — do what you can to become the innocent party. If you send a bad text message out, you’ve got to have a good alibi cooking for the next morning. Always have a good alibi.

I’ve hit a bit of a dry spell, and I’m worried my next date will turn into nothing more than a one-night stand. How do I keep the brakes on?

One-night stands tend to happen when there’s too much alcohol and not really a connection between two people.
People will call each other if they want to hang out again, and if they don’t really like the other person then they just get really drunk and go with the only reason they’re on the date in the first place. So just be sure that while you’re on the date, you stay sober for a good part of it and figure out if you actually enjoy the person, before you go dancing or somewhere else where the social liquidity would increase.

I’m having a guy over for dinner as a second date. What can I cook that will impress him, but not come off as too much effort?

Typically guys, their favorite food is something simple. It’s something like, mac and cheese. Or pizza, or pork chops — it’s not chicken tenderloin de la sol. And if you can cook a simple dish like his mother cooks it, it’s awesome. It’s hot.

Morgan, 22

How can I incorporate sailing into the bedroom?

To be a good sailor you’ve got to be good with knots.

The guy I’m seeing wants to take me sailing on a date. What should I know before I go?

First of all, know how you handle being off-shore, or figure out where you’re sailing, because a lot of girls I’ve taken sailing have gotten sea-sick. That’s not necessarily a dealbreaker, but it can be embarrassing for the girl. Also, I’ve taken out a few girls who have shown absolutely no interest in learning the ropes. So it’s nice to show that you’re interested in the same passions they’re interested in.

What has sailing taught you about dating?

Half the fun is enjoying the actual trip. It’s not just getting from point A to point B.

Things got crazy one night and I slept with a coworker. What can I do to avoid rumors or awkwardness at the office?

Oh boy, I’ve actually had a lot of experience with this on the boat. Well, never trust that that one coworker can keep their mouth shut, because in my experience sharing with the one person you trust is sharing with the whole boat, or the whole office. Certainly, the fewer people who know, the better.

I’m having a guy over for dinner as a second date. What can I cook that will impress him, but not come off as too much effort?

If you have to bust out a cookbook, you’ve probably gone too far. Unless you’re completely unfamiliar with cooking, in which case that’s probably not the best way to his heart. Something from your old standards. You don’t want to try anything new because that always has room for error. That can definitely be entertaining, but at what expense?

I’m loud in bed, and my boyfriend keeps thinking I’ve orgasmed when I haven’t. I don’t want to hurt his pride, but how do I let him know he hasn’t given me an orgasm in three months?

You certainly don’t want to be quiet in bed, because that’s half the fun. Keep telling him that you’re almost there, and don’t let him think he’s accomplished it — give him verbal confirmation when you’re getting close as opposed to just being loud and making him think he’s got you there.

Zainab, 23

The guy I’m seeing wants to take me sailing on a date. What’s the one thing I should know before I go?

Your purse can double as a barf bag.

Things got crazy one night and I slept with a coworker. What can I do to avoid rumors or awkwardness at the office?

Deny, deny, deny. Just don’t talk. Never talk about it. Don’t become awkward and start avoiding eye contact and leaving the room when that person shows up.

I’ve hit a bit of a dry spell and I’m starting to worry my next date will turn into nothing more than a one-night stand. How do I keep the brakes on?

Take care of it before you go out on your own. And keep the alcohol consumption to under two drinks — that’s what I have to do.

After a one-night stand I thought went decently well, I found out it was the girl’s first time. I don’t see us dating. What do I say to let her down without messing her up?

Be completely honest and forward and don’t chicken out and ignore phone calls or whatever. Just tell the girl you think she’s great and that you’re glad you guys met. You shouldn’t say, "We should just be friends." That’s probably the worst thing you could say. Cause you’re not gonna be friends.

I’m loud in bed, and my boyfriend keeps thinking I’ve orgasmed when I haven’t. I don’t want to hurt his pride, but how do I let him know he hasn’t given me an orgasm in three months?

You tell him. Because if you’re not honest, you will become way too attached to yourself. If you’re not honest, you’re not going to solve the problem. And his real pride’s going to come from knowing that you’re actually having an orgasm. Just lay there after and say, "Well I hope you enjoyed it." And then when he asks if you enjoyed it, you say, "Yeah, but I didn’t really come. Thanks." Or you drop a hint and you go, "Maybe next time I’ll have an orgasm."

What makes a good blowjob a great one?

When it ends really fast.

Ben, 23

https://benjoseph.org

Why should I try to get with a sailor?

We’re usually in pretty good shape, we’re pretty tan, and we’re pretty laid back. We can take you out sailing, which is probably the best in ever. Especially in New York, I have access to boats up here and it’s an amazing first date. It works so well. You gotta get the sunset right next to the Statue of Liberty — oh my gosh.

What’s the best way to get into a sailor’s pants?

Any kind of rum drink. I’ve cut back recently, but when I was sailing on regular basis in high school and college, we did drink pretty heavily on a regular basis. Get ‘em drunk, because it’s usually pretty easy to do.

Things got crazy one night and I slept with a coworker. What can I do to avoid rumors or awkwardness at the office?

The best way is to just take it head-on, just take control of the story. Acknowledge it: Just be like, "Hey, you know, it happened." Be up front about it and move on quickly.

I’m loud in bed, and my boyfriend keeps thinking I’ve orgasmed when I haven’t. I don’t want to hurt his pride, but how do I let him know he hasn’t given me an orgasm in 3 months?

Subtle behavior modification — we hate asking for guidance, but hints and direction are always appreciated. Don’t make an intervention out of it — sitting the guy down and having a heart-to-heart about how he’s not pushing your buttons is the surest way to crush him. When you’re in bed, just be more explicit. Say, "I’m almost there." It’s good if you’re loud, but you should also be specific. Guys don’t want to admit it, but we like direction in bed. We’re just not going to ask for it.

What makes a good blowjob a great one?

Enthusiasm. Maybe I have too much empathy, but I can’t really enjoy it if it doesn’t seem like she’s into it.

Interviews by Meghan Pleticha. Dating
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