Guide to Holiday Hookups

Dear Dategirl,

I’m a recently divorced, middle-aged woman and am facing a problem that has me quite bothered. I work with a man who I’m very attracted to, and I think the feeling is mutual, because we’re both incredibly awkward around each other.

We have both been hurt in the past, and I think maybe we are just afraid of rejection and/or not being rejected and then maybe getting hurt again. How do I know for sure? I was someone’s wife for so long, I don’t know how to “date.” I get the feeling that he is in the same place, but how can you really tell what another person is feeling? Especially when we work together and see each other only on a professional basis?

When we first started working together, I was certain he was attracted to me. Suddenly he was in my part of the building all the time, and we had projects together often. We work well together but also have a large portion of our jobs that puts us at odds with each other, but we seemed to make this work, too.

But lately we seem to be moving backward instead of forward. I must have done something wrong. I don’t want this to continue, but I am afraid if I approach him about it, he will be scared off or not respect me. What do I do?

Scaredy-Cat

As I pondered your situation between glasses of eggnog, I got beaned in the head by an antique glass ornament Inky the kitty swatted off my extremely festive tree. Extracting the shards of glass from my eyelashes, I had a revelation: It’s the most wonderful time of the year! Lucky for you, it’s Office Christmas Party Time! Newly single or not, you know what that means, don’t you?

Well, I’ll tell you—the office Xmas party is license to drink until you vomit, act like a jackass, and feel up that hottie from accounting with absolutely no chance of recriminations the next day, because all of your co-workers have behaved just as badly as you, if not worse.

So slide into your finest low-cut corporate casual, slap on a little extra lipstick and eyeliner, and grab yourself a cocktail. Let yourself go. Have fun. Flirt. Corner him behind the cubicles and maybe give him a wink or a quick flash of hot boobie action.

Though that’s the best advice you’re going to get, I’m betting you’ll ignore it. So I’ll let you in on a little secret: Nobody worth dating is actually any good at it, and everyone’s scared of getting hurt.

After I got dumped by my most long-term boyfriend, I was absolutely convinced that nobody would ever want me again. To prevent myself from getting confirmation on what I considered a fact, I retreated into my own little fortress of solitude. Eventually, I got sick of the self-pity party and started to put myself out there.

And what happened? I got hurt. I made huge errors in judgment and slept with far too many men I shouldn’t have wasted latex on. I made an utter fool out of myself countless times. Gallons of tears were shed. There were STD and pregnancy scares. Nights spent curled in the fetal position. Months wasted pining over various idiots whose names I can’t even conjure up these days.

The result of all that heartache? A weekly column and a book that a well-adjusted person couldn’t have written. Oh, and a pretty nice boyfriend, too.

So yeah, putting yourself out there can be scary, and you’ll probably get hurt once or twice, but it’s a lot more fun than sitting home alone, feeling sorry for yourself. Once you accept the fact that you’re probably going to get kicked in the ass (and surely a divorce is more painful than some knucklehead declaring that he doesn’t want to go out with you), I bet you’ll have a much more festive outlook on things. One last tip: a necklace made of mistletoe. Ho, ho, ho!

Dating dilemmas? Write Dategirl at dategirl@seattleweekly.com or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.