Tag Archives: first time for everything

First Time For Everything: The Great Twentysomething Move-Out

As Erin already pointed out, there will be some point in your career as a twentysomething when someone will break your heart. There’s also a chance you’ll break someone’s heart. Either way, there’s a good chance that someone will be your roommate, making cutting ties an even bigger bitch than usual. Here are the dos and don’ts of breaking up with your live-in boyfriend from girls who’ve done it. Keep reading »

First Time For Everything: Dating A Good Guy

I have dated losers of all stripes. Degenerate gamblers, pathological liars, cheaters, guys who can’t get it up, nymphomaniacs, older guys, younger guys, short guys, out of shape guys, steroid-pumping in-shape guys, musicians, baby daddies and waiters. I even had a brief affair with a Voice Over Artist. Yes, in a world where you can’t find a boyfriend, you have sex with a man who reads out loud – for a living.

Totally shockingly, in this vast, impressive portfolio of Y chromosome mediocrity, I have always ended up with the shit end of the stick. The common thread that weaves all these winners together (deep-seeded dysfunction aside) is the complete ambiguity that defined my relationship with each of them. We dated, often for months on end, but was he my boyfriend? I would be plagued with the flogging inner monologue of a quiz show – question after question after question. What was he doing when he wasn’t with me? How come he drinks so much? Why does he smell like Chanel No. 5 when I wear Stella McCartney? And where did all those track marks on his arms come from?

You know, typical pseudo-girlfriend type worries. Keep reading »

First Time For Everything: The Rebound

After a bad break-up, I hid in my room for a while listening to Beck’s sad Sea Change, clutching my childhood stuffed animal, Muffin, wondering what I did wrong. But after the obligatory period of self-pity, I was ready to move into phase two: the drunken rebound. My newfound freedom had me wanting some free love! So I rounded up my lady friends, put on my please f*** me pumps, and went out just to get back out there.
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First Time For Everything: Losing The V-Card

I will forever associate my virginity with toads. No, this is no allusion to fairy tales, no delusions of princess-like grandeur. To my grave disappointment, at no point during my epic virginity-losing did the pimply faced amphibian straddling me morph into a dashing prince. The reason I associate my deflowering with toads is because instead of a Bon Jovi ballad or a sweet Sarah McLachlan serenade, I lost my virginity to the unlikely ribbits of toads.Namely those in that famous Budweiser commercial – you know, BUD. WEIS. ER.

Romance, bitches, is not dead. Keep reading »

First Time For Everything: Having A Baby

It was like out of a dirty dream: I was lying on my back on a stainless steel table completely naked when the door opened. Owen Wilson walked in with a large white sexy toy looking thing, wearing a lab coat. He looked so hot I could barely stand it. As he walked near me he started to talk…

“Hi Kate, my name is Dr. D.”

Oh that’s right. No, I am not lucky enough to be having a sexual role-play encounter with Owen Wilson. I am pregnant and seeing my OB/GYN (who happens to look and talk just like the You, Me, and Dupree star) for the first time. A girl can dream though right? Especially when the reality is as unexpected and bizarre as any nighttime mind wanderings.

Dr. D explained to me why he was holding what appeared to be a massive sex toy; it was an internal ultrasound machine, which would allow him…me…to see the baby. As my lady parts (the parts…the position, that got me in this situation in the first place!) were being poked and prodded, I began to contemplate how the hell I got here. Keep reading »