Dating Advice from . . . Polar Bears

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The Coney Island Polar Bear Club is the oldest winter bathing organization in the United States. The club swims every year on New Year’s Day and every Sunday from October through April. Visit them at

Louis, 54

How can I tell my boyfriend he doesn’t have the body for a Speedo?
Holy Christ, they’ve been trying to get me to wear a Speedo! I’m married thirty-two years and I have two of these European-style Speedos. I won’t wear them. If he’s got any sense of pride, he’ll know he can’t wear it either.


How about for a woman? Is there a tactful way to tell a lady she’s losing her bikini figure?
Holy Christ! That’s grounds for homicide. I would maybe say something to the effect of, “Maybe you’re showing a bit too much.” But I probably wouldn’t even touch that. That’s shaky ground.

Would you recommend a cold swim for a hot date?
No. It’s too much stress. It’s not for everyone. Women, in my experience, take to the water better than men. I had new women come down in the last few weeks who’ve stayed in the water as long as I have. If you go for a cold swim with your boyfriend and you stay in the water longer than him, that may start some negative vibes. He may be thinking of it as a macho thing.

I’m engaged to a wonderful man, but I feel like I didn’t date enough during my prime. Sometimes I fantasize about sleeping with other people. What should I do?
You’re not ready. Put the wedding off and sow your wild oats.

What’s the best reaction to an unexpected “I love you?”
What kind of “I love you” is it? Is it an I love you I love you? Because I’m Italian. I love everybody.

Let’s say it’s serious, from someone you just started dating.
You’re going to have to say “I love you” back.

My eighteen-year-old brother has been seeing the same girl for four years. She’s manipulative and I’m worried that he’s never going to see what else is out there. How can I tell him he needs to land more chicks?
I see this over and over and over again. I have three daughters, and one of them was in that situation for seven years. I see it more with these young kids, fourteen to twenty, going with the same guy, getting beat up on. Sit down and have a heart-to-heart with this kid, tell him that this is really not healthy.

What’s the best to pick up a Coney Island Polar Bear?
Well, we’re very, very heavy. First, say something complimentary about what he or she looks like coming out of the water. Then, on the way back to the clubhouse, ask them out.

Capri, 54

I’m going to have sex on the beach. Anything I should know?
You definitely want to put something underneath you, because that can get really nasty. Sand is tricky stuff. Either that or just go in the water. Sex in the water is the best — you’re like a fish. Or it’s like in a waterbed, except that in a waterbed it takes awhile, depending on how much water is in it. I never could get the hang of waterbeds. Have you ever been on a waterbed?

Years ago, I had a waterbed. My boyfriend and I used to get into these wild arguments. He was always throwing stuff. So we were having one of our crazy arguments and I thought, “You know what? Fuck it. He’s always throwing stuff. I’m going to throw something.” So I picked up a coffee mug and I threw it against the wall and it shattered and went all over the waterbed. It made all these tiny punctures. That was my last time I threw something in a fight.

My boyfriend and I are strapped for cash. How can we plan a cheap romantic evening?
God, you could do anything. You’re making love to the person, not the situation.

How can I tell my boyfriend he doesn’t have the body for a Speedo?
In a very diplomatic way. Maybe flip through some sports magazines and say nicely, “Wow, that guy looks good, maybe you could strive for that.” But at a cold swim, I overheard two guys talking. They said their members hurt, and they discovered that if you wear a Speedo it keeps it close to your body. If you’re hanging free and easy, it’s actually very painful.

I used to appreciate that my girlfriend spoke of her ex fondly, but I just found out that he’s really attractive, and now I feel insecure about it. Am I the just nice guy she’s seeing until she goes back to him or to some other handsome man?
First of all, it doesn’t sound like she’s completely over her ex. She has to let go of that past relationship and be completely with you. Some people are jealous about exes, but me, I’m still friends with all of my exes. We’re still in touch, but I would never get back with them romantically.

My boyfriend’s brother just told me that my boyfriend is what is known as a “chubby chaser.” Not only am I creeped out by the idea that I’m fulfilling some fetish, but I’m also offended because I don’t think I’m that fat. Is there any way I can stay in this relationship?
So it was just confirmed that you’re a butterball. That’s awful. Women have enough trouble with their weight as it is. To hear that he’s only with you because you’re a porker, that would make me feel so bad. Ask him: “Honey, do you love me or my fat? Would you still love me if I turned into a toned athlete?” And a lot of weight problems have to do with self-esteem, so it could also be that he’s only interested in women who dislike themselves.

Is it okay for a girl to have mainly male friends when she’s in a committed relationship with a guy?
To me, it’s a myth that you can find a person who satisfies your every desire and need. In a healthy relationship, you have other people who satisfy your other needs. I’m a musician, and every time I join a band, all the girlfriends and wives come and check me out. Once they realize I don’t do that, they say, “Yeah, you can hang out with my husband or boyfriend.” And I think that’s healthy.

I’m a reasonably attractive woman with a great personality, but whenever a man approaches me I come off as boring. How can I get better at flirting?
You probably are boring if you can’t put any interesting tidbits out there in five minutes. You have to go fishing, you have to put interesting stuff out there, so someone will say, “I’d like to find out more about this person.” Some women talk all about themselves all the time, and it comes off the wrong way. You’re probably talking to much “me, me, me.”

My friend just started dating my ex-boyfriend. There’s this particular weird sex thing my ex enjoys that I know will totally freak her out. Should I give her a heads up?
No, let her find out. That’s the thing about being in a sexual relationship — it’s about exploring and finding out each other’s desires.

Dennis, 50

My boyfriend told me too much about his sexual past. Now I see his ex around and I can’t shake the idea of them together. How can I get over this?
When you ask a question, you may get more than you bargained for. Participate in the relationship you have. Everyone’s got a history. Everyone has had sex with more people than just you. That’s just the real world and if you want to know about it, ask, and if you don’t, that’s okay. But you can’t act as if it doesn’t exist.

I am an alright looking lady with a great personality, but whenever a man approaches me I come off as boring. How can I get better at flirting?
Why do you want to? I think some of the most interesting people come across as boring at first. I’m not one for flirting myself. I’m familiar with the rituals and the practice, but I do think there’s some value in maintaining your distance. People will see that and become interested in you.

How can I tell my boyfriend he doesn’t have the body for a Speedo?
Who does? Anyone who wears a Speedo knows what they’re doing. So many people are uncomfortable with their body in public. I’m six-four. I’m not a bodybuilder. I don’t look good on the beach. But at one point in my life I realized there’s nothing in it for me to be uncomfortable with my body. So you may catch me in a Speedo one day.

Lou said he owns two Speedos, but he’s never put them on.
He could pull it off. And if they don’t appeal to me aesthetically, that’s my problem. I wouldn’t dissuade anyone from being comfortable.

I met an amazing woman two months ago, and we’ve decided to move in together, even though our relationship is still new. Bad idea?
I don’t see a compelling reason to commit after two months. A relationship doesn’t have to be locked down immediately to be fruitful. What damage could be caused by slowing down a bit? Continue to pursue passionately with everything you’ve got, but don’t lock it down right away.

I’m engaged to wonderful man, but I suddenly feel like I didn’t date enough during my prime. Am I not ready for marriage? Or is this just cold feet?
If you go into a relationship thinking you’re missing something, you’re always going to be stuck with that. If you really feel you need more experience before this, then it would be wise to go get that. You may find out otherwise, but you’ll have to live with that.

I’m planning on having sex on the beach. Anything I should know?
Sand is an abrasive. There’s also sunburn to consider, unless of course you do it in the winter. And it’s not crowded — just cold, so bring a blanket.

"Iceman," 51

I want to have a really interesting first date. Would you recommend a cold swim?
Yes. Cold swims can heat things up. You get to see if they’re outgoing individuals and you see how they look in a bathing suit.

Speaking of which, how can I tell my boyfriend he doesn’t have the body for a Speedo?
Make him look at some pictures of himself.

And if I were having the same problem with a girlfriend?
Break it a little more gently.

I’m a twenty-one-year-old man who’s attracted to mature women, but I’m not interested in just being a boy-toy for some hot housewife. How can I get an older woman to take me seriously?
You have to work on it slowly. You should meet them in a non-threatening environment — museums, galleries, things of that nature. That way you’ll get to meet them and know them first, and they’ll get to know you.

What should I include in my online personal ad and what should I leave out?
Include the basics: age, area. Leave out the wild things and the very intimate items — in the real world, you don’t know everything about someone when you meet them, you don’t want people to know everything about you.

What’s the best way to get a Coney Island Polar Bear to go home with you?
Get neck-deep with them in freezing brine. 

Interviews by Kate Sullivan. Sex Advice From… appears on Thursdays. Have questions for the general public? Send them to

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