I believe there is no rhyme or reason when it comes to how relationships start. Being in my 30's and single I float between two groups of friends--my married ones, and my unmarried ones. I've bartended for about five years at a boutique hotel in Midtown, so I’ve had more than my share of relationship talks with all kinds of women. My biggest take-away: the right person will like you no matter what. Which brings me to the seemingly timeless question, "When should I sleep with him?" My answer: do it when it feels right. If that means on the first date, then so be it. It’s not 1950--you are not easy if you sleep with a guy on the first date, and it’s not going to ruin your chances of being with that person.

One of my friends slept with her now-husband on their first date, and they’re now about to have their second child. I have friends that wait forever to the seal the deal and then are surprised that the guy didn't stick around, as if there’s some kind of formula for keeping a guy interested. I have a roommate (male) who was dating a girl in a her early 20's who was doing the "I'll make him wait so he'll respect me" thing--but I find the idea that there’s a correlation between how long you keep your underwear on and how much men respect you to be way old fashioned. You command respect with your personality, not your vagina.

I think the first hour or so with a given guy can tell you most of what you need to know about how he’ll treat you. You'll know if sleeping with him right away is a mistake--it's just up to you to listen to that intuition. Again, I want to throw out this idea that sleeping with someone on the first date makes you easy. The entire concept of easiness makes sex entirely a dude’s prerogative, where sex depends on how successfully he can convince this passive creature to “give it up.” I mean, please.

Categorizing women based on when they choose to fuck guys is dumb and wrong and way outdated. Your timing around sex doesn’t dictate who you are as a person. Do what makes you feel happy, because that's what is a turn on. Shame around first-date sex is such a double standard--I have never thought less of guy if he slept with me on a first date, so why should we do this to ourselves? You know when a toddler is walking around and then he trips and falls? Well, a good way to prevent them from having a meltdown is for the adult to not act like it was a big deal. The toddler will cry if the adult gasps and makes it a big deal. So if you sleep with a guy on a first date, don't make it a big deal, because it isn’t. (I'm saying men are big toddlers.)

One big advantage of first-date sex: you can figure out what this person is into sexually. What if you saved yourself for marriage (bear with me) and on the night of your honeymoon you find out that the only way he can climax is by choking you. What a bummer! Sexual compatibility is a huge part of a healthy relationship. What people are like in the bedroom can be way different from what they’re like in other parts of the house. I once dated this guy that people seemed to think really highly of, but the first time we had sex he was abusive, and not in an S&M way. It was a big red flag and I ended it the next day. If I didn't have sex with this guy when I did, I wouldn't have known this about him and would have spent way more time and investment on someone who was definitely not worth it.

When it comes to dating and being in control of your sexual self, always focus on your needs and wants and the rest will fall into place. The best way to stay balanced is to focus on one thing--your own happiness. Just be safe and always carry condoms!

By Sarah Tollemache
You know that saying, "You're born alone into the world and then you die alone?" Well, I've also been spending a lot of alone time in the middle, mainly at Chipotle. While alone in the middle I make witty observations and wish I could quit Facebook.


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