Tag Archives: first time for everything

First Time For Everything: I Called Off My Engagement

Recently, I committed the ultimate relationship taboo: I told a man who wanted to spend the rest of his life with me that I couldn’t marry him. Even worse, I broke off my engagement at a time in my life when many of my close girlfriends are blissfully picking out wedding dresses and drafting tender vows of love to their soon-to-be husbands. Welcome to your late twenties, ladies.

During my engagement purgatory phase, when I’d finally gathered enough courage to share my indecision with a few confidantes, I was met with a collection of theories on how I would know if my fiancé was “the one” or not. After the jump, find out why all the nuptial advice I got amounted to a load of courtship crap when it came to my relationship. Keep reading »

First Time For Everything: Dating A Younger Man

I have forever dated older men. Some by a year. Others by four years. Another by ten years. My theory came to be that ten years might be the ideal age difference. I felt five years older than my age, and men were usually about five maturity years younger than their actual age, so if I was 25, my ideal mate would be 35. We would meet at the figurative age of 30. It all made perfect mathematical sense. Keep reading »

First Time For Everything: Holiday Party Hook-Up

There I was at my first company Christmas party, looking respectably sophisticated in a little black dress and kitten heels. Fresh out of college, I was working a coffee-running, “Ugly Betty” kind of job at a major conglomerate. This seasonal shindig wasn’t your average corporate affair. Since there were thousands of employees, no one was allowed to bring a date, and it was held at a big dance hall with a giant disco ball hanging overhead. The whole event was like a prom for work people. I huddled among a circle of girls from my group, trying not to watch my supervisor shake it on the dance floor. Keep reading »

First Time For Everything: Shacking Up

You truly don’t know your man until you perform the ultimate test of compatibility. No, it does not involve signing up on eHarmony.com to see if you’re meant to be. To know if your love will last until the end of your days, you must do the inevitable: Move in together.

When my boyfriend of a year and I considered signing a lease together at the beginning of this year, the prospect of living together was a dream come true. I, like many other women, naively thought shacking up was the natural first step to happily-ever-after. Through my rose-colored glasses, I envisioned our bond strengthening and our relationship evolving. Best of all, we’d be together all the time.
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First Time For Everything: Sex On The Beach And Other Unlikely Places

Everybody’s talking about British psychoanalyst Brett Kahr’s meaty new tome, Who’s Been Sleeping in Your Head?, based on the largest study of sexual fantasies ever undertaken. Not surprisingly, sex in public ranks high up there. This very important research prompted me to take an oh-so-romantic walk down memory lane to reflect on what were the worst, and best outside of the bedroom sex experiences my slutty self (and “friends”) have indulged in. Some were hot, and a few may illustrate why the best sex is sometimes confined to the sack.
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First Time For Everything: Dating A Grandfather

Last year, I had sex with a grandfather. That sounds bad, but I didn’t know he was a grandpa until after we’d done it. Plus, he’s a good thirty years younger than my own grandfather. But still, at 53, he had two kids and a baby granddaughter, while at 32, I’m itching to give birth to my own babies. When he confessed his real age to me over lunch following our hotel-room hookup (he’d told me he was 48), I assured him that I didn’t mind.

And at first, I didn’t. Part of what attracted me to him was that he was mature. He owned his own home, had a secure job. His life wasn’t as precarious as the other guys I’d recently dated. He seemed steady and solid, thoughtful, and I liked the idea of him presiding over a family. It made me feel like he’d be protective and gentlemanly, but still hot. Keep reading »

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 »

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