Love Lola: Break-ups, hook-ups and re-entry

Dear Lola,
This Christmas my manager is having a work party at her house and inviting the whole staff. After closing the store, we're going to order tons of food, drink and play games all night. She's already told us that we're all welcome to stay the night so that no one needs to pay for a cab. I have the biggest crush on a guy from my work and I think this is the night that I should tell him except I don't know what to say; HELP!
Christmas Crush


Dear Crush,
There's only one thing worse than a drunken holiday sleepover with co-workers and that's a drunken holiday sleepover with coworkers where some drunk girl cries.

Aside from what's sure to be a wickedly unprofessional, taboo, Facebook-documented evening, you do have to return to work with these people on Monday so let's try a reality check; does this guy even like you? Don't pretend that you don't know. If you think he's into you, then you really don't have to walk up to him and say; “Hey Bob, I like you.” Just dress cute (not slutty), bring a yummy snack and stay sober enough not to embarrass yourself. This night's intimate set-up is the only “move” you should need.

If you don't know if this guy's into you, then guess what? He's not. Men aren't as complex as we wish they were; there's rarely a hidden agenda or a “secret crush” in a man's life. If he's into you, he'll let you know by hanging around you, making you laugh and using way too much Axe.

The worst case scenario from a night like this (other than a sexual harassment lawsuit) is that your “big move” will be rejected and you'll wish you could go back in time and warn yourself to keep your big mouth shut. So let this be a message from future you to present you; don't do it. Let things develop naturally. This night could be the beginning of something really special. Or possibly the night you get to see your boss toss her cookies in a poinsettia after too much eggnog.

Either way, just don't be the crying girl. It's Christmas for Pete's sake.

Dear Lola,
I've been dating a nice girl for about eight months and it's been going okay. There's nothing “wrong” with her, but I just don't feel that spark. A few months ago, we bought these super expensive tickets for a New Years event in Toronto and I really want to go. We already have hotel and dinner reservations and a bunch of our friends are coming too. The problem is; I know I want to break up with her. I'd rather do it after New Years so that I still get to enjoy the night, but I just don't want to spend Christmas with someone I'm breaking up with. She wants me to meet her parents and I'm sure she's expecting a gift. This feels like a disaster; please help.
Merry Miser


Dear Miser,
Christmas is a time of joy, right? Well, congratulations on sucking the spirit out of the festivities honey. You've managed to strip this holiday of any nostalgic, peaceful, childlike wonder and have made it all about strutting your stuff at some T-dot club.

You actually think a girl might “expect a gift” after eight months? Dude, you have got to be the worst Christmas boyfriend ever. Your priorities are so messed up right now! Forget about commitment, honesty or loyalty; a brother can't spend New Years alone! All you're thinking about is the money you “wasted” on this girl's tickets and wondering if there's possibly enough time now to find a replacement date who will go Dutch. Yes my friend, you are a disaster indeed!

So according to you, your options are either; break up now and spend New Years alone or keep her hanging on, but have to spend the holidays with her? Wow. These are some tough choices for a young man to face. How about you deal with this relationship in a polite, respectable manner and try to be truthful and upfront about your feelings? Do it soon. You don't want to leave this poor girl to explain your absence to her whole family when you don't show up on Christmas morning. Oh, and try to break the news before her parents have bought you a gift, okay?

As far as New Years goes, I think you should just take a buddy and have a wild Vegas-style boys night in Toronto.

Better luck next year.

Dear Lola,
I'm going home for Christmas for three weeks after exams and I just found out that my ex will be home too. We dated all through high school, but grew apart at the end of last year and decided to break up when we were going to different colleges. He knows I'm coming home (we've been talking on Facebook) and he wants to hang out. I've been super focused on school this year so I've had a bit of a “dry spell,” so I'm pretty eager to spend some time with him. How wrong is it to hook up with him over the holidays and then head back to school in January?
Focused, but Frisky


Dear Frisky,
Interesting the way you worded that question: How wrong is it? Clearly you already know you're acting inappropriately so I guess I don't have to say it. Measuring the “quantity” of sin in one's actions is a pretty complicated task, but heck, I'm up for it.

Stirring up old feelings without the intent to follow through? 5 Sin Points!

Planning a holiday hook-up when you're supposed to be spending time with your family? 10 Sin Points!

Risking pregnancy and disease to get a little action? 15 Sin Points!

You'll need to decide for yourself what you're comfortable with, but I try to stay below a 35 on most occasions.

Truthfully, if your ex is into it, I think it sounds nice! What else are you supposed to do for three weeks? Just don't get sucked in with all the twinkling lights, ice skating and hot cocoa; I'm assuming you broke up for a reason so try to keep a level head when reentering the playing field. Hey, as long as you didn't break up over his erectile dysfunction I say go for it!

Happy Holidays!

Letters to Lola

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