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I told him I wasn’t interested in a relationship – but now I’ve fallen hard. How can I convince him to give us a shot?

  • Author: Wayne and Wanda
  • Updated: April 28, 2018
  • Published April 28, 2018

Dear Wayne and Wanda,

I have known "Jack" for many years. Several years ago, when we were both single, we started meeting up. Usually it would be late at night, and one of us would simply go to the other's place and stay over. We have a lot of friends in common but we didn't tell anybody this was going on. It was very casual, which worked for me at the time. I had gone through a bad breakup and wasn't in the right mindset to jump into anything serious. Still, a couple months in, he had asked me if I wanted to grab dinner or drinks, and at the time, I reminded him I really wasn't ready for anything serious and really appreciated we could just hang out and be low-key.

I think that hurt his feelings or at least his ego because his texts stopped and not long after I saw on Facebook he had a girlfriend. It stung a little and felt like he had rejected me (even though I guess I rejected him). Fast-forward to about six months ago, and I deduced from changes on Jack's Facebook page that he was single. So was I, so not long after, I went to the restaurant where he worked to say hi, and that led to text messages between us, which finally resulted him coming over a few nights later, and we basically picked up where we left off.

I'm in a much better place now, and pretty quickly realized, I really like Jack, and not just physically. I like how I feel around him, and I like how he thinks, and his sense of humor, and I love hearing what he thinks about things. When he comes over, I find myself stalling to say goodbye, hoping he will stay longer. I look for reasons to text him throughout the day and get sad when he doesn't reply immediately. Realizing I've got a massive crush on him, I decided to revisit his invitation from several years back. The last time he came over, I asked him to go on a real date with me.

Jack's response surprised me. He said he's grown and matured and he realizes now as two consenting adults, we can casually hang out without having to feel obligated to elevate it into a relationship status. He said just like I was going through that breakup years ago, he is in a similar space now, and for that reason, was excited to spend time with me because he knew there would be no expectations. He said he doesn't want a relationship and was attracted to me again knowing I'm "the same as him."

I don't know what to do. It's true I didn't want to date Jack three years ago but I was going through a lot. Now that I do want to date Jack, he doesn't want to. I feel like I screwed up my one shot with him. I want to think I can change his mind and convince him to give us a shot. Can you give me any advice?

Wanda says:

Lady friend, you are facing an ages-old problem: is it possible to turn a hook-up partner into a boyfriend? Many people have started down the path of casual sex feeling emboldened by the no-strings, carefree nature of it all, only to surprisingly find complex feelings have formed. Inevitably, one of the players almost always develops more intense feelings and finds they simply don't want to play around anymore: they want to make things serious. Often this is the female half of the equation, thanks to the release of a certain evil chemical called oxytocin that makes women feel warm and fuzzy and overly-bonded to our partner. Darn chemistry.

So here you are, and now in Jack you apparently have an unwilling partner in romance who would love to continue being a casual partner in bed. What to do? You aren't necessarily doomed. It's true that you and Jack have an established pattern and patterns are very hard to break. You may be locked into FWB status for life, no matter how charming, lovely and persuasive you are.

But there could be hope. From your telling of events, it sounds possible that Jack thinks you asked him out because you thought that's what he wanted. Following me? Try again. And make it very clear that you're asking him because you're into him, like a lot, and that you respect he's going through a tough time and that you like him so much you're willing to go slow or even wait for him. Make it completely, crisply, irrevocably clear that you are crushing on him hard and you want to give the two of you a true shot.

Wayne says:

Look, I don't know Jack … No really, I never met the guy. But I'd bet that he just isn't into you like that anymore. And, sorry, he might never be again.

It's not that he's harboring any ill will, bitterness or resentment about your dating diss. If he didn't like you, he wouldn't have started hooking up with you again. But I'm sure you did hurt him, and it forced him to accept how you felt about him and shift the way he felt about you moving forward. Having some space from you and dating other people probably solidified that for him. In fact, after your recent restart of hookups, I bet he was shocked to hear you ask him out on a real date. That might even run him off again.

Now that we're clear on Jack's feelings, I'd really like to know how you truly feel about him. You've got a big-time crush on the guy now, but he's basically just been your hook-up buddy, a status you've made very clear in the past. What's changed? Why did you seek him out when you found out he was single? It wasn't because you wanted to date him; you wanted your FWB back. So are you sure that he's your Mr. Right and not just your Mr. Right Now? Something to think about …

Either way, so much in life and love is about timing. Sure, you can occasionally will things to happen with a little luck, hard work and charm (like getting him back to your place shortly after your surprise restaurant pop-in). But ultimately, if the timing isn't right for a relationship, it just won't work. Sound familiar? Maybe the planets will align for you guys in six weeks. Or six months. Or six years. Or never. But don't wait to find out. Go with Wanda's advice — if this is what you really want, make it clear to him and see what unfolds.

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