One Step Forward, Two Steps Back

arrow-1043850_1920Back in December, I left a detail out of my story because it was embarrassing, but I want to share it now. It’s still embarrassing, but it illustrates a larger point.

A few days before my 36th birthday, I found myself getting broken up with at an Indian restaurant. I had seen it coming, but it still stung a bit, as break-ups are wont to do. In a moment of desperation, I told The Teacher that I’d still be interested in a no-strings friends-with-benefits scenario…effective immediately…like, can we go back to your place now? We didn’t end up sleeping together that night, and I texted him later to say that I had been shortsighted and didn’t think a FWB arrangement would be wise. He said he understood and wished me well, and I never saw or heard from him again. The next day, I wrote a post called Rejection Reflection (it’s one of my favorite posts) and came to the  following conclusion:

I don’t think that I was meant to function this way, to partition my heart — one half cautiously hoping to find love and the other biding its time until the inevitable end. But it feels reckless to do otherwise. If I operate fully in the hopefulness, I am completely vulnerable…. Whenever I see a tightrope walker perform, I’m impressed, but there’s something uniquely spectacular about one who walks the wire without a safety net. I think dating is a lot like that. I’ve been walking confidently, knowing that the nets were there. But that’s not how I want to live.  I want to trust myself enough to boldly approach inherent risk. And that’s what a romantic relationship is, right? A risky fucking endeavor.  Here’s to being intrepid in the face of danger, my friends.

Why bring this up now? Well, I spoke with The Leo last night after my spider senses began to tell me something was up. He jumped straight in with providing the clarity I wanted: he thinks I’m great, loves spending time with me, but he wants to make sure he’s not leading me on, as he’s not looking for a relationship right now. Basically, he’d be happy to continue with the status quo (seeing one another every other weekend when my kids are with My Ex, staying in touch via text during the week), but he’s not looking to be a boyfriend. This was not unexpected — we’d had a similar conversation early on in our non-relationship, but let’s be real: similar to what I posted yesterday about dating culture, almost everyone claims to be looking for casual. It’s a self-defense strategy that cuts both ways: when things don’t work out, it’s not a huge deal because you were “just casually dating,” but when one of you catches feelings and it’s not entirely mutual, the unaffected party can just claim to be surprised that your heart’s involved because “I thought we wanted to keep things casual.” So yeah, everyone wants things to be casual…until they don’t anymore. It’s the paradox of casual dating: it’s all fine and good until someone gets too attached. I’m not saying all that to imply that I had gotten overly attached to The Leo, but I keep running into this phenomenon, and I needed to vent.

Back to my point. My immediate response with The Leo was gracious understanding, agreement, and relief at having a clear picture of where we stood. But when I woke up this morning, something felt off, and I knew I had to make a choice.

Choice 1: Stay the Course

I really enjoy spending time with The Leo. He’s a genuinely good person, we have amazing chemistry, and no matter what we do, the time flies because we have so much fun. But that’s all it will ever be. It’s easy. And comfortable. It’s walking a tightrope with the promise of a nice springy net below. It’s the opposite of what I said I wanted for myself. It may also be the best-case-scenario that I can reasonably expect based on my current life circumstances. Because I fear I was right all those months ago when it occurred to me that I was undateable. It was a truth that I accepted calmly at the time, but now it brings a lump to my throat. Hunting unicorns is for children, right? Sure, but there’s something about staying the course that feels distinctly like settling for less than what my heart wants.

Choice 2: Resume the Hunt

So if I don’t want to settle, if I want to honor my resolution to embrace an inherently risky activity (putting my heart out there, asking if anyone could possibly consider loving me — I practically hyperventilated just typing that), then I need to walk away from The Leo. Despite how much I like the nets he offers, my days of dating multiple men at a time are over. But if my underlying belief about my undateability is true, then I’ll probably keep finding more of the same: great guys who may eventually want to put their hearts on the line, but not with me, not now.

Choice 3: Call It Quits

This is always an option, I guess. Just live my life. Fuck companionship. Fuck casual relationships. Fuck romance. Fuck dating apps. Fuck.

I knew back in December that sacrificing my dignity for temporary pleasure wasn’t a good choice for me. It’s how I know that Choice 1 would be problematic. Just writing this blog post has been an exercise in heartbreak. I don’t like any of these choices, and I’ve been going through my day on the verge of tears because it feels like I’ve come so far only to be knocked on my ass by reality. In re-reading the excerpt above, though, I can’t help but notice the words I chose: “I want to trust myself enough to boldly approach inherent risk.” I guess if this all boils down to trusting myself, I’ll be ok. It’s all the other unknowns that have me feeling decidedly less than bold.



10 Comments Add yours

  1. erinmedley says:

    I relate to this all too well. What I find most amusing about guys who aren’t ready for a relationship is that even when keeping things “casual”, they are most definitely in one. If you are texting someone every day, seeing them when you can and dating exclusively, how is that not a relationship? It’s just a lame excuse that gives men an easy out when they want one, completely discounting our feelings as though they — or we — never really matter. And who knows, maybe we didn’t, but it’s still a really shitty way of treating another human being.


    1. fortymatches says:

      Agreed. What I described with The Leo is a relationship, except it intentionally lacks heart. “Keeping things casual” is like playing in the shallow end of the pool. It’s safe, and you get a taste of what it’s like in the water, but it’s nothing like diving into the deep end.


  2. If The Leo will not make a commitment, that does not reflect on you. That is The Leo making the decision not to be more. Leo wants to keep his options open and that’s not fair to you. In my experience a FWB always leads to heartbreak. I believe option 2 is best. Cut communication and let go. It may be difficult but will allow you to find someone else.
    When I first got divorced, I remembered thinking to myself, No one is going to want me. I’m 27 with two kids. What woman will want a guy like me? But there was one out there. I found her.
    There is a person out there for you as well.


    1. fortymatches says:

      Thank you, James 😌
      I think you’re right. I did end up letting him know last night that I didn’t think that the status quo fit with my vision of what I wanted for myself. We parted on good terms, and I cranked up my dating app profiles again. 27 with 2 kids is tough. Try 36 with 4 kids. I’m not on anyone’s wishlist. My cynicism is on overdrive right now, but I haven’t resorted to choice 3 yet, so I guess that means I’m holding onto hope that you’re right and I’m wrong. I’m so glad you found your person!!


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