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Ask Jess #9! Did I Ruin It By Sleeping With Him Too Quickly?

Posted by
Jess

Dear Jess,

I am just going to dive right in.

I went out on three dates this weekend. Two awful dates on Friday night, and one great date on Sunday. As a result of the two awful dates, I got a little overexcited on the good date – as did he.

I ended up sleeping with him. On the first date.

Can this be salvaged? We already made more plans, but I am skeptical. Can I still turn this into a relationship?

Love,
Overexcited Ollie

Dear OO,

These are the Ask Jess’s that I most love and fear. The ones where I will refuse to give you a straightforward YES or NO answer, because that would involve lying and oversimplifying the sensitive dynamics of your situation.  The truth is, sometimes the answer is just…it depends.

So let’s get to it.

First of all – good for you, going on so many “dates!” Might I assume that you’ve been online dating? We’ll leave that question unanswered for now.

The fact of the matter is that by sleeping with this guy on the first date, you did nothing wrong. Based on your apologetic “Crap, how do I fix this?!?!” tone, I can tell that you’re torturing yourself and falling prey to a harrowing mix of strict societal (and personal?) expectations about female sexuality. But guess what? You’re a modern, grown-ass woman, and you made a decision that felt right at the time.

Whether it was motivated by attraction, or excitement, or relief after your bad dates – it doesn’t matter! Stop beating yourself up. Sex is fun. That’s why we do it. No regrets.

Now, that said…how can you expect this to affect your relationship with the new guy?

Here’s the truth.  For better or worse – both you and I have no way of knowing. Yet. The rules about how people are supposed to react to this are no longer universal, or even dependably predictable. He could be an old-fashioned, quick-to-judge traditionalist who instantly threw you into the casual hookup category after that first night. Or, he could be an enlightened, open-minded free thinker who had a great time and is excited to see how things progress with you, in and out of the bedroom.  Both guys exist in droves these days.  Don’t assume that he’s either/or at this stage in the game.

The only way to find out? Continue hanging out with him! Which should be easy, seeing as you guys ALREADY HAVE PLANS! And unless they revolve around meeting up at 2am on a Saturday night (which strikes me as highly unlikely, given that you wouldn’t really call those plans, right?), my guess is that he is interested in continuing to get to know you.

On that note, why the needless skepticism? If a guy says that he wants to see you again, and puts in the effort to confirm a time and a date, then we ladies should take him at his word and approach the whole situation with a positive attitude. Don’t doom the relationship with unnecessary guilt and neuroticism before it even begins.

Of course, this isn’t the first time that we at WTF?! have delved into this question of engaging in, um, premature sex – and determining the fallout on a burgeoning relationship. Our very first (!) hotly-debated guest blog, Ruth Bader Sinsburg’s Why Lust May Just Lead to Love, introduced the topic from the perspective of a sexually empowered woman who has launched several long-term relationships from seeming one-night stands.

And what was the takeaway message from that post, other than that Ruth Bader Sinsburg is my idol?

That we don’t all feel the same way about this issue! Look at the comments! Try as we might, we haven’t all found common ground – male or female. At the end of the day, in this era of romantic ambiguity and transition, it’s all based on what YOU believe and how YOU expect women to act.

So don’t panic. You did what you did, and there’s at least a 50% chance that he’s (more than) fine with it. He may even be thrilled that you’re so confident in your sexuality!

Yet next time, I would suggest holding off on having sex for a longer period of time – not because it will make a guy like you more, but because you should always be sure that you’re honestly ready, and not going to wake up in disaster mode the next day.  If you can’t own it, then you probably shouldn’t do it.  But again, that decision should be based on whether you feel ready and comfortable enough, and not on how you think he’s going to react.

Because if you’re both dying to have sex, and then he can’t handle it the following day, then he’s just not the right guy for you.  Period.  And instead of trying to convince him otherwise, you should just wait for the guy who’s going to embrace your healthy sexuality and relish in the opportunity to rip your clothes off without waiting a requisite number of days, weeks or months.

But in this case? Relax, hang out with him again, and see where it goes!

WTF?! BOTTOM LINE: Stop being mad at yourself. Don’t assume that you’ve ruined anything. Hang out with him again, as planned. And trust your instincts on whether he’s still treating you in a respectful, “Girlfriend Material” way. If he is? Then continue on!

Now that I’ve hopefully (non-)answered your query, I have to take you to task for a moment.

You went on one good date with this guy, yes? So why are we already talking about “turning this into a relationship”???

Whether this was the date of your life, or of the century – a date to make even those hasty lovebirds Lamar and Khloe jealous – it’s too early for you to be throwing around the word “relationship,” even in your head. Fantastic that you like him. Fantastic that you felt comfortable enough to sleep with him. Fantastic that you already see long-term potential there. But that’s where you should pause for the moment.

It’s been ONE DATE! If your connection eventually blossoms into a relationship? Beautiful. But no one should be actively “turning” a spark into anything else, much less a full-fledged relationship. You guys barely know each other. It’s too soon. And this is why so many guys think all women are “crazy,” and why we’re gearing up for Crazy Girl Week here at WTF?! (yep!).

I’m not saying that you are crazy. I promise, I’m not! My brain is fully capable of making the same drastic jumps through time and space when I meet a guy who I really like (see the description of your Boyfriend Prospect, and the inevitable daydreamy ski weekends that occur in your mind when you’re around him, HERE).

But this is where your brain has to override your heart for a bit. Focus on the next date that you two have planned – and not on what dish set you’re going to buy when you move in together. Don’t make the all-too-easy mistake of instantly equating sex with love and commitment – at least until you spend more time together, and YOU can be sure that you truly like him. Enough to put a Relationship label on things.

He’s the awesomest guy in your gaggle. He’s your Boyfriend Prospect. Leave it at that for now.

Sep 16, 2010
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