Hi Katherine,

I’m 5’11” and in good shape but I’ve been on a dry spell for over a year and I have been unable to fix that. My main question is: how do I build flirtations with new girls that I meet if there really isn’t a perfect way to shift things to a more intimate setting? Sometimes schedules don’t align and there’s barely time for more than a quick glance.

This one woman I met online last week, I find her attractive and I would love to find a way to flirt with her (text or a quick date could work) but I’m in my head about the sheer effort of breaking the ice and the anxiety of what could go wrong if I approached her incorrectly.


Dearest JB,

The weather’s getting chillier and the stakes are getting higher as every ship rushes to find a port to spend winter. Breaking the ice is the first step. It’s a challenge that’s tormented vessels mightier than yours or mine. Consider the following advert, allegedly posted by legendary Antarctic explorer Sir Ernest Shackleton in a London paper at the turn of the century:

“Men wanted for hazardous journey. Low wages, bitter cold, long hours of complete darkness. Safe return doubtful. Honour and recognition in event of success.”

One could say the same of the kind of fortitude required for a journey of the heart (and loins): In-laws are the polar bears of the domestic sphere, a botched opening line is as daunting as spearing a seal and a misinterpreted text can make an icy chill settle in the pit of your stomach. The journey of romance can be dark and cold; the hazards grow more plentiful with the added complication of an online dating interface; but yet, we all do it anyway.

The great irony is of course that even after such an unappealing ad, Shackleton ended up with plenty of companions to choose from. Lust for honor will always thaw the hearts of men; so will just plain lust. One of Shackleton’s voyages trapped him and his crew in ice for 10 months, nearly the length of your particular dry spell, my dear JB.

If he braved icepack and freezing water to save all 27 members of his crew, I’m confident you’ll be able to break through the ice of an initial encounter.

Here’s how:

Chill Out.

You seem quite preoccupied with approaching women the “right” way, but truthfully, there is no such thing. Warm up to the idea that it may not be perfect. A stranger once asked me out at 2 AM in a grocery store by telling me I had a “very American face.” Given that our nation’s only coherent physical reference is an obesity epidemic, I should have been offended. But it turned out that he was incredibly charming and we had a great time. In fact, we ended up making out in jean jackets outside a pizza shop. (How American.)

Break through.

If this is an online flirtation you’re dealing with I would suggest cutting to the chase sooner-rather-than-later and asking her out. Be witty and persistent in getting to an IRL encounter, my dear. Cordial persistence pays off. Here are some obstacles you may encounter:

You text: Wanna hang out on Friday?
She texts: I’d love to. Parents r in town. ;-(
You text: So… I guess you’ll be needing multiple drinks then?

You text: Wanna grab a drink tonight?
She texts: I’d love to but it’s 15 degrees outside and snowing and I’m on the couch.
You text: Hot toddies?

You texts: Nice running into u today, wanna go for a walk on Thurs?
She texts: Great seeing you too. This week is really tricky with work, rain check?
You text: Oh… what do you do exactly? I don’t think you told me.

That being said, some Ice Queens can’t be melted.

Some people hate when others take an interest. A friend of mine admitted to cringing “anytime anybody appeared to read one line of my profile and say something like, ‘I see you are a filmmaker. I also like movies!’” When pressed, she said she preferred people who incorporated irony or humor into an initial message (her favorite being the time a gentleman she knew in person saw her profile and wrote simply, “Oh Dear…”).

Let the thin ice crack.

Let me ask you, what is the worse thing that can possibly happen when you ask this lady out? Visualize it happening in gruesome, humiliating detail. Now, remember that Shackleton’s crew ate stewed penguins for breakfast. Every day. For six months. Whatever happens won’t be as bad as that.

Be your own captain.

At some level many of us believe we are too complicated or ugly or sad to love and be loved. Remember that you’re not. The sooner you believe that the easier it will be to ask a lady out and the sooner this dry spell will become a deluge.

Don’t look back on ships passing in the night.

I set people up on dates for a living, and sometimes I think of myself as a glorified secretary. Half my time is spent negotiating hectic New York City schedules. Here’s what I have to say: if somebody doesn’t have time to see anybody more than once a week they’re not actually interested in seeing people. If schedules keep missing each other then, to quote Frozen’s Elsa, “Let it go.”

Avoid deep-sea diving.

Even Ernest Shackleton himself had limits. He famously turned around when he was just 97 miles away from the South Pole rather than risk the lives of his men. If you find yourself plumbing the depths of your crush’s Facebook profile and starting to “like” photos from 2003, it’s probably time to pull back. There is a fine line between obsession and interest. Know when to extract yourself.

Revive yourself from hypothermia.

As you move from digital to IRL, have a plan for when things go wrong. Sometimes things just ice over on first dates: You’re awkward, she’s late, and the food at the restaurant is bad. Any chemistry has crystallized in frigid silence. The best thing to do in this case is simply acknowledge how badly things are going. A simple “Let’s start over,” can really warm things back up. (See other first date tips here.)

Find your Endurance.

Endurance was the name of Shackleton’s famed ship, but it’s also an essential virtue to cultivate. Look, the worst that’s going to happen is that you’ll get rejected. Keep going. The secret to romance as well as exploration is finding the ability in yourself to endure, even when it seems impossible.

Over the course of his life Shackleton was knighted, awarded a gold medal by the Royal Geographical Society and has inspired countless books, films and shows. The journey of love and lust is bitter, cold and long dear JB, but I have every confidence that you too can be the stuff of legends. If Shackleton braved the ice of Antarctica four times, I’m sure you’ll have at least that number of breakthroughs on the tundra of romance.

Just the Tips is Playboy.com’s weekly advice column, with professional matchmaker Katherine Cooper. Have a question for Katherine about sex, love or dating? Shoot her a note at justthetips@playboy.com.