Q: I met this guy about 5 months ago and we agreed that we were both not ready for a relationship (him just getting out of a serious relationship and me not ready for one at all). So we began having casual sex, but that stopped when he got back together with his ex. Now that they have now broken up again, we have both admitted to having feelings for each other and have thought that there might be something else between us other than just casual sex.
Does the fact that we know each other so intimately hinder our ability to get to know each other better on a more relationship-oriented level? I know that I am interested in him, and I know he is interested in me. But I want to build what we have beyond a purely sexual relationship. Is that possible?
A: The short answer: Yes. The long answer: It depends on a variety of factors.
First off, it depends on how long it has been since both of you ended your last relationship as to whether or not what you've got now has a chance. Since it sounds like the gentleman in this equation is newly-single, that alone might be reason enough to hold off for a bit -- both in having casual sex, and in trying for something more. Give the guy a bit of time to recover. Let him process what's just happened properly, so he's able to partner with you intentionally when the time comes.
Next, I'd want to know if the two of you have spent any time together outside of the bedroom. I'll assume you have, or else neither of you would be wondering if a potential relationship was on the horizon. So with this in mind, I'd strongly suggest spending more of your time doing things together that are more 'date' activities, and leave the casual sex off to the side for now. Do you need to stop having sex? That's up to you. But the danger here lies in reveling in your sexual chemistry and not really exploring who each other is outside of a casual sex relationship.
As well, the fact that the both of you weren't ready for a relationship when you met, but now are because these 'feelings' have come up, is something to discuss more. What has changed since you met, other than time? Are you sure that both of you are ready for another relationship, independently of the fact that he's just gotten out of one? Many casual sex relationships start because one or both partners aren't able or willing to commit, yet long for physical intimacy without the emotional attachments. Although I realize its hard to determine whether or not the guy you're interested in has commitment issues this early on, perhaps take a look at your own for now, to see whether or not this is a theme and how it might affect the two of you dating.
Finally, I'd want to know whether or not either of you would flinch when telling others how you met. Will you have to lie or edit the truth somewhat? Will the story be different for your friends, coworkers and family? Discuss this with your potential partner casually when you get the chance, and see what he has to say. If nothing else, it'll spurn some great conversation, and you'll get a better idea how the two of you will respond to conflict and challenges in your relationship.
All of this information isn't meant to sour you on the idea of moving from casual sex into a full-blown relationship however. I've worked with countless couples whose relationships started with casual sex and moved into something more. It can happen, it does happen, and sometimes even with great success. The two of you are off to a great start having communicated your interest in one another. Keep on communicating openly, talk about where you'd like for things to go, and spend some time together outside of casual sex -like encounters. Soon enough you'll both have enough information to determine if something more is really there.
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