Dear Jess,

I have been sleeping with this guy for about six weeks. First it was casual, but now, it’s five or six nights a week. He spends the night at my place almost every night, and also hangs out during the day for hours at a time.

We still have never gone on a date or met each other’s friends, but I’m starting to think this could go somewhere. Casual sex is one thing, but spending all your free time together is another – and it’s obvious that we’re genuinely enjoying each other’s company.

I should mention, though, that immediately at the beginning, he made it clear that it was just sex, and claimed that we didn’t have a “relationship connection.” At the time, I was cool with that. He’s not the type of guy I usually date, and I thought we’d just have fun for a while and then go our separate ways. But instead of our connection fizzling, it feels like it’s gotten stronger with time. The more we hang out, the better it gets.

But, he did say that. I can’t ignore it.

The truth is, I’d like to at least try dating him. Whatever that means. Is there any hope for this to become more? What should I do?

Thanks,

Sexing in San Antonio

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Dear Sexing in San Antonio,

First things first – you asked if there is any hope for this situation to become more. You’ll be pleased to know that the answer is yes! YES. Yes, yes, yes. No guarantee, of course. But is there hope? Absolutely.

I have a feeling that someone in your life (or your trusty knowledge of typical dating mythology) might be telling you otherwise. Starting now, tune this peanut gallery out. Anyone who can’t see the potential in these play-non-dates-turned-more is coming from a dangerously old-fashioned romantic perspective, and is probably also wondering why this guy hasn’t offered you his pin and varsity letter jacket yet.

I can call out this potential so confidently, and encourage you to stay hopeful despite the untraditional elements of your courtship that would leave other dating gurus shaking their heads and putting you in the time out corner, because of my research for Dating & Hookup book. I heard versions of this story many, many times throughout my interviews with men, women and couples – and surprisingly often, the tales turned out pretty great. People hooked up. People navigated murky waters. People fell in love. But of course, there is a sort of art to that particular romantic trajectory.

Let’s break it down.

Meet Your New Role Model, Eva

Sexing in San Antonio, you remind me of a girl who I interviewed in Portland, Oregon named Eva. I want to share her love story with you, because she once found herself in an incredibly similar place. And if you can see how Eva cultivated her own relationship and adopted a healthy perspective to cope with the ambiguity, you might find some guidance for how to move things forward with this guy in your life.

Eva’s story begins with her meeting a guy at a party. Simple. Typical. Has happened to all of us. And then, in her words:

“I stayed over the first night we met, and it was really cute and awesome and beautiful and moving. But he immediately said to me, ‘Listen, I don’t commit to anything, and I don’t have any intention of this lasting.’ Of course, I was anxious about that. But then I thought to myself, okay, this is going to be as long as it’s going to be. And I’m just going to enjoy it until it ends!

So, I just kept enjoying it. And after that, we hung out every day – and it was HIM calling, saying, ‘Can we see each other?? Can we see each other??’ And things just changed. He stopped being scared of factoring me into his plans, and we went on to be a couple without even saying anything about it. He’d never had a relationship like that. Now it’s two and a half years, and I’m the happiest I’ve ever been in my life.”

P.S. – they’re now married. Cute, right?

Here is what Eva did – and Sexing in San Antonio, this is what I would like you to do as well.  Eva focused, above and beyond anything else, on enjoying her time with her guy, and cultivating and strengthening their connection. She focused on that connection more than she focused on the labels and definitions about what they were doing.

Literally every time she got anxious about what they were doing, or what it all meant, she shifted her focus in a more fundamental direction – she thought about how they could enjoy their immediate time together instead. Because, you know, their time together was going to end…any day now…or so she thought…

That was it. When in doubt, connection trumped labels. And that moment-to-moment, feeling-to-feeling focus eventually developed – much to both parties’ surprise – into a beautiful, committed relationship.

Now, let’s note that part of the reason Eva was able to stay so levelheaded was because she was valuing and investing in other parts of her life while she was navigating the ambiguous dynamic with her guy. At the time, she was genuinely psyched about her photography, and some classes she’d just started taking, and the new friends she’d been making lately – so she wasn’t putting all her effort into tricking this guy into falling in love with her, or basing all her self-worth on whether he’d texted her that day. She was viewing this relationship as just one part of her generally fulfilling, meaningful, exciting life.

Do whatever you need to, to make sure that this connection doesn’t end up consuming all your thoughts and time. Only then will you be able to give it the time and space it probably needs to flourish – and stay happy, sane and respectful of yourself in the process.

Of Course, Don’t Be a Doormat (but I Don’t Think You Are!)

To be clear, I am not (not not not!) telling you to settle for sleeping with some guy who you actually want to date, just because that seems to be all you can get from him. That sounds awful and emotionally disastrous. But who says that’s what’s happening here?

If he were booty calling you twice a week at 2am and jumping out of bed first thing in the morning, that would be one thing. My advice would be very different. But from what you’re telling me, he’s not. Five or six nights a week?! That’s a lot. I can’t remember the last time I hung out with anyone five or six nights a week. Even Becky. We would kill each other by Night Four.

That is a substantial amount of time, and not the typical Last Resort/booty call protocol. And for your time together to be both at night and during the day, both sexual and casually fun…well, that’s just good. That’s the sign of a guy who is enjoying spending time with you. Guys don’t spend that much time with girls because they have nowhere better to go, or nothing better to do. They could always go home and catch up on their Fantasy Football stats. Men are pretty talented at finding excuses to run away, when they want to. So, safe to say he is enjoying spending time with you, in different types of ways and settings. Sweet.

But Then Whyyyyyy the (Lame, Premature) Disclaimer??

Usually I’m a fan of believing the words that come out of guys’ mouths. They say they don’t want a relationship, then, they don’t. And I bet your guy meant it when he said it. So, WTF?! And why did he even bother going there and shutting down that possibility so soon?

The fact that he said it so immediately, and before knowing what type of connection you actually had, makes me think that it might’ve had less to do with you, and more to do with his perception of relationships. And therein lies your opportunity to shake up that perception for the better.

Why might “relationship” be such a dirty word to him? Hard to say without knowing him, but my guess is that he’s heard some pretty terrible things about relationships. Today, all of us hear terrible things about relationships – especially men. Maybe he’s had crazy exes who made relationships painful for him (this was the case with Eva’s guy)…maybe his parents split up in a traumatic way…maybe he watches too many sitcoms and thinks relationships are lame and boring like on TV…maybe he has buddies who pressure him to be out on the town every night…who knows. But he’s heard something about what “a relationship” is like, and he thinks he doesn’t want one. Cue the premature disclaimer.

Fine. But the possible solution? Teach him what Eva taught her guy – that actually, a great relationship is just two people who never stop connecting and never stop enjoying each other’s company. Maybe he doesn’t know that relationships don’t have to be complicated and restrictive and regimented. Maybe he hasn’t realized yet that he’s already halfway in one. It sounds like all he knows right now is that he wants to be spending time with you. So he might just need some more time to acknowledge that – duh – wanting to spend time with someone is not very far off from wanting to be in a relationship with them.

This is why I say, just, you know – carry on. For now, try not to think too much. Focus on enjoying it all.

THE BOTTOM LINE: This has potential, if you can continue having faith in your connection. These days, labels are often the last piece of the romantic puzzle to fall into place. So as long as you’re hanging out almost constantly and growing in your relationship, don’t stress about them quite yet. Instead, every time you feel anxious or are thinking too hard about what you guys are or aren’t, focus on the fun and the connection. When you feel that worry, switch gears and say to yourself, what fun thing can we do instead? Watch a movie? Get some food? Make out? Maybe finally meet up with some friends? Like Eva, decide to enjoy whatever it is you two have, until it ends – and then stop worrying about when that end date will come. If the connection is truly special, then maybe it never will.

The Caveat

Okay, so there’s a caveat here. Amidst all this talk of connection and enjoyment, there’s the possibility that someday soon, you might stop having fun. You might become so worried about the labels, or about the question of exclusivity, that you can’t truly enjoy the time you two are spending together. At that point, it’s time for a Talk.

(Again, if you’re actually having a great time, and are just worried about what your friends and mom are saying, then ignore them and keep going. But if it’s really starting to get at you, and there’s suddenly more stress than enjoyment on your side of the dynamic, then, Talk.)

You could rely on the typical, slightly scary Talk questions of “what are we??” and “are you my boyfriend??” and “what do you want from this??” and “at what age do you see yourself having kids??” Or, here’s another option: you can get into the conversation by addressing the sexual exclusivity of your relationship. Which is obviously completely in your right to discuss. Isn’t there a new STD popping up like every day?

Would you feel safer in your connection, and more confident in your dynamic, if you knew that maybe you weren’t in a “relationship” yet, but that he also wasn’t running around banging other chicks? Then hey, start with that. Tell him that your sexual relationship has become special to you, which has led you to feel uncomfortable with the idea of him simultaneously having that relationship with other people. Trust me, if he’s spending five or six nights a week at your place, he probably won’t be very surprised to hear this anyway.

Once you bring up the question of sexual exclusivity, you’ll quickly get a sense of how he’s seeing your relationship and how he’s feeling about you. If he’s willing to forego other potential connections for you, then, great. Solid step in the right direction. And if he’s not, then – ouch, goddammit – at least you’ll know where you stand and can make an informed decision about whether you want to stay involved with him (since you have feelings for him and would be explicitly settling for less than you want, my vote would be NO – but, your call).

Point is, if a Talk feels necessary, then I’d suggest starting off with a chat about your sexual exclusivity and moving forward from there. For some guys, “relationship” is a big word. “Boyfriend “ sets off alarm bells. But “in order to keep sleeping with you, I need you to stop sleeping with other girls for now?” Labels aside, a guy who feels truly connected to you and is developing stronger feelings for you will have no problem giving that a whirl.

Image courtesy of dougbelshaw.

PS: Have a question for Jess? Email it to [email protected]!

PPS: Want more? Read a free excerpt of Jess’s book Dating & Hookup HERE!