“I’ve never even kissed a woman,” Adam said. One of my best friends on the planet, Adam was unequivocally gay—the kind of caricature personality who lisped, wore pink, plucked his eyebrows, flicked his wrists, and decorated his apartment in rainbows. He was my first call when a guy I was dating was being a jerk, the one who was always up for an impromptu shopping mission or who’d dance with me until the wee hours of the night at an ‘80s club. Technically, he was everything I’d want in a boyfriend: smart, funny, kind and gorgeous—too gorgeous to be straight, as the saying goes. But since he was gay, I barely noticed.

But as he said those words, our faces were inches apart and we were locked in that trance-like pull of an inevitable kiss. We were at a party, dancing to New Order. And soon our lips locked and we were full-on making out. As I felt his hands squeeze my butt, I backed up and stared at him. “You’re an amazing kisser,” he said, with a wink.

Next thing I knew, we were back at my place.

We met when I delivered his mail, a task performed by all the interns. But I liked to think I was different: I was an eager little NYU journalism student, desperate for attention, and I chatted with all the editors as I passed their cubicles. Many magazine editors on the top of the masthead are a bit standoffish and see interns, especially ones who want to talk while they’re busy, as an annoyance. But the Older Man was actually inquisitive and kind; we’d chitchat a little bit, a welcome reprieve from the other editors who could be cold and snappish. 

As a single lady who has lived in a big city for years, and now moved to a new one, I’ve had my fare share of one-night stands. I’d never call myself someone who makes a romantic life out of having a lot of random sex. In fact, my heart stands more on the traditional side where I look for sex after the relationship connection, knowing I usually wind up hurt in casual flings and that I actually disdain the thought of adding another one-nighter to my “list.”

When I first set out to write about swinging for an article about the lifestyle, the last thing I expected was to find myself nodding when a slim, curly-haired brunette asks if she may take off my panties. It’s a windy Friday night and I’m in a cozy, apartment-style swing club in Midtown Manhattan, my short, cherry-red dress folded down to my waist—all in the name of research, of course. The bartender, a curvy blonde, leans over to kiss me.

I thought I’d had “rough sex” before; I’d been spanked on my butt plenty of times, had my hair pulled, even been caned once while strung up with my hands over my head. That hurt, and I cried, and I liked it, because I’m submissive like that, but it was just a one-time thing. I’d had plenty of encounters with talking dirty, spinning all sorts of nasty fantasies, where, most of the time, I was on the receiving end of some very hot epithets. But I’d never wanted to be choked until I got together with the guy I’m dating now.

My first spanking was at my 16th birthday party. My guy friends tackled me on the kitchen floor and took turns giving me 16 spanks. And maybe one for good luck. I don’t remember. Once freed, I was livid. I was mortified.

And I was totally turned on.

It began with my high school English teacher. I was 15 and shy; he was 30 and moonlighted as a poet. He also cursed in class, horsed around with his students, and (despite his age) still had jet black hair. I got nervous and sweaty whenever we interacted, and my childish crush raged until high school ended. I visited him while I was home for winter break, but when he mispronounced my name and forgot which university I attended, my puppy love subsided.

“So when can we meet him?”

This is a question that most women long to hear from their friends after dating a great guy for a couple of weeks. It is the last thing you want to hear, however, when your current beau is unattractive. Alright, I am sugarcoating it—this guy was ugly. Now, please hold your judgment; I have always prided myself on being able to look past a pretty face and see a man’s inner hotness.

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.

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. 

I consider myself one of those lucky girls who lost their virginity before college. I had a typical high school experience; I wasn’t a “queen bee” but I wasn’t at the bottom of the food chain either. My high school boyfriend and I mutually “swiped” each other’s v-cards at sixteen. He was my first love and blah, blah, blah. We decided to stay together even though we were going to separate colleges. It worked out great for the first semester and the mind-blowing, “can’t wait till you take your clothes off” sex every time we saw each other definitely helped the situation.

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.

I really didn’t know what polyamory was until I fell into it at 27. I was arguing one day with a couple I’d been sleeping with for about a month, when BAM! I ended up in a three-way relationship.

I’ve always been open-minded as far as sexual relationships were concerned and was sleeping with a male/female couple. That day, Dan was being overly critical of Ellie. I told them the nit-picking was bothering me, but it really wasn’t my business how they treated each other, since, you know, it was their relationship.

That’s when they looked at each other and asked me, “Well, aren’t you kind of… with us?”

Hmm. “Fine,” I said to Dan, “Be nice to my girlfriend then.”

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.

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.

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.

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.

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 #&@$% 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. 

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.

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.