The Gentleman's Guide To The Holiday Hook-Up

You two have been making eyes at each other since at least September. A fair amount of your “professional” relationship has been spent playfully flirting. As fate would also have it, you both happen to be single right before Christmas. The universe is telling you only one thing “Go for it.” However, do keep this in mind: the fun part about this relationship is that it’s secret. Also, be realistically minded: the spark will fade after the holidays come and go. My advice to you is have fun and then move on. Believe it or not, she’s probably thinking the same thing. So, how exactly do you go from co-workers to co-spooners?

1) Be Corny

It’s the holidays, you have license to look a little bit like Jimmy Stewart on a sugar binge. Don’t be afraid to use a simple, yet obvious, gesture to get things started. For example, buy her that Kanye West album she’s been waiting for all Christmas. Do something that is, in fact, genuine, but actually shows you’ve been listening to her.

2) Play Your Advantage At The Office Party

There’s a good chance she’ll look for a real person to talk to while her boss is on a cougar hunt. Play the part of “fake boyfriend” to ward off advances from others and commit to it: establish physical contact, make her laugh. When you two are talking, notch up the flirting a bit. She’ll note your confidence and your chemisty points will soar.

3) Do Something Together, Non Work-Related

Specifically, something that seems innocent, but could really go either way. Getting a drink, seeing a movie, do some Christmas shopping. Find an opportunity in the days leading up to time off – or on the first NIGHT of time off – to see each other. You’ll both be away from the office and the fate of the night is in your hands.

She just got done with finals, and she’s smart enough to know: you spend Christmas at home and New Year’s in the city. She’s also got a month and a half of free time to kill. Guess who she’s looking to spend it with? The College Girl is an interesting speciman: if she wanted to be with another undergrad, she would’ve done so already. She’s looking for an older guy because she thinks age equals maturity. She also thinks that 25 is “Like, wow!” This is where you doing a little research on Pitchfork will pay off in dividends. Plus, having anything to say about a book she just read for Women’s Studies doesn’t hurt, either.

1) Don't Try To Hard

This is a girl who gets a lot of b.s. thrown at her. Granted, what woman doesn’t, but do you remember what you thought impressed a girl in college? That she’s talking to you already is a sign of interesting and that she’s eyeing you as some “older, sophisticated” guy. So, just don’t try so hard.

2) Drop Some Knowledge

This girl is going to be looking for signs that you’re a serious-minded, “real” guy. Talk about stuff that a “serious-minded” guy would talk about, in other words – anything. You would be surprised what you can sell to a woman if you just employ a sense of confidence. Whatever you do, don’t make the mistake of trying to please her.

3) Work Only When You Have To

At some point, she’s going to want to show you how for real she is, that’s when she may actually suggest going to go see a foreign flick or an art gallery. For the sake of not looking like a jerk, just bend to this point. It’s only an hour out of your time. When she asks your opinion, be honest. Once again, if you just give any kind of confident credence to you, you would be surprised what happens.

The Easiest Mood Killer Of All

So, I’m guessing you know this by now… well, I hope you know it by now, but I’m going to tell you anyway: don’t confuse a hook up for what it is. Yes, it is the holidays and everything is festive and exciting. But, do recognize that anything happening between you and whoitsface is not plausible grounds for a relationship. This goes especially for any kind of office romance. The risk is just too great professionally and emotionally. I know this sounds like a buzzkill, but I’m talking a) from experience and b) from common sense. Nothing ruins the memory of a great hook up like a couple of weeks of calls, e-mails, and a few “coincidental” run-ins at places like bars and front doors. It’s not worth it, dude. It’s the holidays. Have fun. And don’t worry about making it last. The whole point is making the most of your time. Not obsessing over morning sex and Chinese take-out.

Check The Links

Jackpot. She’s beautiful. She’s fun. And she’s gone by January 3rd. Back to Wisconsin, or wherever. The Out-Of-Towner is the best option you could have asked for during the holidays. Consider that she’s only in your city in the first place to have a one-of-a-kind holiday. What better way to cap that than by hooking up with a local boy? It’s Christmas magic… in the form of shallow romance! This is the girl who is looking to get swept off her feet. She willingly look past things like job, apartment, police record, because she wants the excitement of saying she was with a New Yorker. As long as she finds you at all attractive, you’re set for the next few weeks.

1) Take Her To Your Spots

It doesn’t matter that you know how to get into the city’s hottest club, she won’t care about that. What you should be thinking about is taking her to places you know, places where you always hang out. The fact that it’s not a tourist hotbed will be exotic enough for her.

2) Be Prepared To Drop A Little Extra Cash

Sorry, Scrooge, but when it comes to the holidays, you’ve got to be willing to spend a little extra. It goes against any rule I usually have, but if you want to keep the holiday fire burning – be an uber-gentleman. That said, don’t go overboard. If dinner at Landmarc is out of your budget, don’t try to make it so.

Tips For The Morning After

The office ice queen. The bitchy neighbor. The obnoxious barista at your local Starbucks. Look, be honest: the only reason that person even gets under your skin at all is because she’s hot. You’ve thought more than once about using a mutual hate for one another to fuel a steamy hook-up. Well, now’s you chance. Sometimes, the holidays are best spent sleeping with the enemy before you both return to your respective voodoo dolls. Use your two best weapons to make this happen: early closing hours and full days off.

1) This One Is Purely About The Sex

Good news: you guys are going to see each other naked a lot. Bad news: don’t expect her to be a sparkling conversationalist. The impetus for this relationship is purely physical. More clearly: you’re both horny and it’s a case of right time, right place. Any kind of social interaction you two undertake is in the name of making the sex better.

2) Yes, She Will Still Hate You

Don’t expect the fact that you two slept together to change the way that she feels about you. If anything, the sex will be a reason for you two to leave off of the hating for a while. But rarely does a series of one-night stands change the relationship of two people. She is not trying to tell you she likes you. She’s just looking for a little affection, and sometimes, people go looking for it in the weirdest of places.