Ugh-Glee

Throughout this project, I have gone out with a one-armed prison guard, a man who's never left Brooklyn, two separate guys who've put me on the phone with their mothers, and a comic book nerd who cracked open his Darth Vader piggy bank to pay for our date. I shared a walk in the park with a Southerner who picked his nose and then tried to hold my hand. A Star Wars fanatic confessed his fantasy of climaxing to the Imperial March. Four different denominations of religious freaks tried to convert me. A man "moved to China" to avoid a second date. I've been stood up, let down, and everything in between. But I still can't tell my crush I'm totally into him.

I know what you're thinking: any girl who can survive 97 (so far) dates with guys who bring everything from cheat sheets to their cats out for coffee can surely bring herself to say to a cute guy "I like you." But it's just not that easy. Perhaps the reason I could go out with a man who thought a night in a hot tub was an acceptable first date is because there was no real risk there (besides being seen in a bikini!) There's no real sense of loss when your date shows you his SpiderMan watch in the first five minutes because you're pretty sure that this is not the long term future you've been pining for. You can tell you're not going to marry the Payless shoe salesman or the guy with a penchant for the original Karate Kid movies or the weirdo who is mysteriously anti-candy corn. These men are not what we call "relationship material."

But what about the man who IS relationship material? The one who captures your interest, your eye, and dare I say, your heart? What about the date where you risk really putting yourself out there, really falling for someone, and potentially getting really hurt?

This is the problem I'm having right now - mustering up the courage to tell someone I like him, someone who actually matters. The courage is only half the battle, the mechanics of doing it are the other half of the dilemma. I need the courage to face the odds, a 50/50 gamble he'll say "Yeah, that'd be great, you're super cute!" OR that he'll reject me outright and I'll be disappointed, embarrassed, and not able to show my face around him again.

Assuming I can gather all my confidence to tell my magical mystery man how I'm feeling, the other issue is how to go about getting it done! My proposals so far have included:

1) writing an email to his boss, brother, and best friend asking if he likes me and if they'd set us up on a "blind date,"

2) facebook stalking him to see where he'll be and running into him accidentally-on-purpose,

3) setting him up on a date with my non-existent girlfriend so he'll be stood up and I'll rush in to save the day

4) breaking out into a Top 40 pop song while he's shopping at the Gap, preferably with a full jazz ensemble and gorgeous back up singers in matching outfits behind me.

Of course, each of these ideas is slightly flawed in that I could

A) get him fired,

B) make the holiday season unbearable with his family & friends,

C) he'll get a restraining order, and

D) I'm not on Glee.

It is in this moment that I realize my fifteen years of dating history never truly evolved past high school. I still want to pass hand-written, intricately folded, scrawly love notes with hearts dotting the i's and flowers around my name. I still want to ask all of his friends if he "like likes" me and wait outside his classroom / locker / sports practice hoping to spot him and have four blissful minutes of inane conversation that will inevitably give me butterflies in the belly for the rest of the day. Maybe I really have been watching too much Glee for my own good, but at the ripe old age of 30, I still can't think of a better way to tell someone "I have a monster crush on you" than breaking out into song amongst preppy sweaters and enthralled onlookers.

There has to be a better way. Ugh!