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Dear SYngle In The City,


I’ve been hooking up with this guy for a few months now and started to develop feelings for him. How do we transition from a casual relationship into a romantic relationship? I want to tell him how I feel but I don’t want to risk losing our friendship. I’m also worried that he just sees me as someone he can have fun with and not a girlfriend type. Any suggestions on how to bring this up to him or how to handle this sitch?

-Hooked Up and Hooked On




Dear Hooked Up and Hooked On,


For a long time (and by long time, I mean up until, like, yesterday), I thought that there were only a handful of ways to meet a Jewish counterpart. You either went to highschool together, you were set up, you met at a wedding or a party-- or you’re related in some capacity.

But, in our generation, with more people going to college and the rise of dating apps, these avenues have given singles resourceful fodder for their relationship quest. And because college and dating apps are more casual by nature, they’ve given individuals room to explore likes and dislikes without the trappings of commitment. That’s not to say these settings can’t lead to commitment, but there’s more leverage to follow a colloquial relationship trajectory rather than a linear trajectory.

What do I mean by linear trajectory? Let me give you an IRL example:

My friend L met her husband on a double date. She knew right away that he was *the one*. They kissed after a handful of dates. They got engaged within the year.

This story, from the surface, sounds effortless. And very well could have been effortless. But because there are no plot holes, no deviants, no caveats, it makes me think that if a love story isn’t effortless then it means it’s not right. Or that starting out as a hook-up, means you’re not right for each other.

We’re fed a narrative from pop culture that the way in which we meet someone is as important as a relationship itself. We’ve romanticized the ‘meet cute’ so much so (think: How I Met Your Mother and A Cinderella Story and To All the Boys I’ve Loved Before), that forming a relationship from a casual hook-up does not fit that fairytale mold and could open the floodgates to disaster. And, in all honesty, it very well could.

But this thinking, that there is one way to meet someone and there’s one path to a relationship or marriage or whatever it is you’re looking for, is toxic. In The Four Agreements, Don Miguel Ruiz tells readers to break any agreement or rule you subscribe to. In relation to dating, some rules I can think of are the following: Don’t kiss on the first date. Wait for the boy to make a move. Blah Blah. None of these rules are truths. There’s no statistic that says you’re setting yourself up for failure if you kiss on the first date or if you make the first move. I’m all for taking things slow, but following the rules doesn’t necessarily guarantee you a relationship.

If you take the dating rules you’ve been fed out of the equation, I truly think there’s a chance at love from a hook-up.

The downside of starting off with a hookup is having to steer the ship into serious territory. Where to begin? I’ve never been in that situation before, but if my two cents are worth anything, I know many couples who hooked up before they started dating and many who ended up getting married. I also know people who ended up heartbroken from this predicament, which is the story you most frequently hear. Couples who started off as hookup buddies aren’t quick to tell people how they really met. And as far as their children are concerned, their parents met the good old fashion way-—at a wedding. But, as I imagine, forming a relationship from a once casual pursuit could come natural or turn into mayhem. The stakes are high. How do you tell him/her that you’ve developed feelings and switch gears from fun to girlfriend material, you ask?

Before anything, don’t confuse comfort for feelings. Physical intimacy may cloud your judgement. In lieu of your default Netflix sesh, go for drinks in a public setting and see how your conversation compares to the one you have in the comfort of his apartment. To be clear: like women, physical intimacy can cloud men’s judgement, too. So, you should probably determine whether or not his feelings are real before diving in too deep.

Secondly, you can be fun and spontaneous and girlfriend material. Those attributes are not mutually exclusive. Like relationships, there’s no one way to be ‘girlfriend material’ or ‘wife material’ IMHO. If the person respects you and sees you beyond the physical arrangement you’ve created, then he might also want to take things to the next level. The only way of knowing is by asking. The thought of losing him might be a hard pill to swallow, but dragging your feelings through the mud will get you nowhere.

And if his feelings aren’t mutual the way you hoped, it might be time to hook off and make a run for it. I’ll be right here holding the exit door wide open for you.


XX B