Dating Don’ts: On Second Shots & Rerun Relationships

Dating Don’ts: On Second Shots & Rerun Relationships

First, a story. A few years ago, I dated a guy I’ll call Jeff. We only saw each other romantically for a grand total of two months, but it was significant because Jeff was the first guy I had dated since the breakup of my engagement where it felt like I finally had let go of a lot of the baggage that comes with that kind of life-altering, trust-shattering heartbreak. I had dated a bit since that breakup, and even had a rocky six-month relationship at one point, but I was still so messed up. At first, dating Jeff felt like a breath of fresh air. I felt much more together emotionally, and he was courting me like an adult, planning actual dates and seemingly not playing any games. On paper, he seemed to have it together — a good job, aspirations, a positive outlook on the world and what he wanted to contribute to it. Physically, the relationship progressed at a much slower rate than I was used to — we only kissed for the first month — and I took my cues from him, convinced that this was a reflection of him taking me “seriously.”

Meanwhile, Jeff’s own baggage started showing up, piece by piece, revealing that the guy who presented himself as having it all together was actually a bit of an insecure mess. One night, we finally had sex — it was quick and awkward. Soon thereafter, Jeff started to become less available — literally and emotionally — and when I called him on it, he said that I was great, but he wasn’t feeling great about himself. Jeff went AWOL for a few weeks and we never had an “official” conversation ending things, but again, it was two months, we’d had poke-poke sex for all of five minutes and Jeff was clearly communicating with his actions what he wasn’t directly saying with his words — that he wasn’t ready to date anyone seriously. I had let go of enough baggage from my previous relationship to not take it too personally, thankfully. Jeff and I stayed friendly after our little romance came to an end, exchanging messages and likes on Facebook, and getting together to catch up six months to a year, so I was somewhat privy to any action in his personal life — there was none, or certainly nothing significant.

Still, there were plenty of hints that Jeff was growing and changing — going to therapy, switching jobs, etc. — and sometimes he would take the time to remark that I looked pretty in a new FB profile photo or compliment a piece of my writing. On occasions where we would meet up for a drink or dinner, our rapport was easy, but decidedly unromantic; I can — and would — flirt with a tree stump if it looked at me sideways, but Jeff was always so restrained and, as when we were dating, I took my cues from him. I had a hunch there was unfinished business between us, but if we were going to tie up those loose ends, he would have to make the first knot, so to speak.

A few months ago, he did. Jeff and I went out for our semi-annual catch up drinks and immediately I could tell the vibe was different. At one point he said that prioritizing his high standards for achievement had gotten in the way of him pursuing relationships with other people. “Like you,” he said. “I look back and I wonder if you’re the one that got away.” That sideways look? He gave it to me.

“You’ve got my number,” I said. “Nothing to stop you from asking me out again.” A few days later, he did.

Jeff and I started dating again and as you might have surmised from the title of this post, it lasted for two months and ultimately ended the exact same way, for the exact same reasons, as the first time around. It was the ultimate example of a Rerun Relationship — a relationship that didn’t work out the first time you tried it, but for some reason, you give it another shot, thinking the sequel will be better. Sometimes, the timing really is right and it’s like the first failed attempt never happened. But more often than not, this second chance is the same shit, different day, leaving you with a familiar bad taste in your mouth. Based on my recent experience, here are a few signs that what you hope is a sequel is actually just a rerun.

1. He/she hasn’t had much dating success since. Jeff really only dated one woman for any length of time in the years between dating me. Their relationship only lasted three months (hey, one month longer than we did!) and she “never got the official title,” as he put it. I know, I know, this douchey aside should have been my first clue that Jeff hadn’t really emotionally evolved, but, well, sometimes nice people say douchey things and I’m great at making excuses for them, so I let it slide. I tend to be genuinely curious about people’s prior dating histories — if those relationships are over, I don’t consider them a threat, just potentially valuable insight — so I asked Jeff about what went wrong. “We fought about me not being available enough for her,” he explained. “She wanted more of my time than I was able to give her.” I’m a bit of a lone wolf, so the fact that Jeff and I were seeing each other just once or twice a week was actually perfect by me, but I wondered about his “availability” in other ways. When we’d dated the first time, Jeff had a very rigid, set schedule — like, his Sundays were mapped out by the hour — and I had a feeling that was a wrench in this Unofficial Girlfriend’s desire for more time together. He wasn’t able to give that time to her, and while I wasn’t exactly looking for more facetime, I started to suspect that his emotional availability hadn’t budged much either. After all, it didn’t seem like he had made himself emotionally available to anyone since we were last seeing each other.

2. One or both of you has an idealized version of the other. The first two months Jeff and I dated made two things really clear to me: 1) He wasn’t ready for a relationship and 2) that was really unfortunate, because he was such a great guy. Our semi-annual meet ups and Facebook exchanges further encouraged this simplistic assessment. Sure, based on his sweet compliments on my profile photos, links to the various charities he was fundraising for and our easygoing semi-annual drinks, Jeff was/is a great guy.  It was easy to forget all of the things that made this great dude not so great to date — his insecurities and his perfectionism, and how tightly wound he could be when those two things head butted against each other — until they started to rear their ugly heads again.

Meanwhile, Jeff wanted a second shot with “the girl who got away,” but he never knew that girl too well to start with, and besides, I’ve changed a lot since then. Not in ways that are easily noticeable — I look the same and I have the same job — but internally significant ways. In the years between Dating Round 1 and Dating Round 2, I’d done a lot of living and growing. I had a couple intense relationships, I dated a lot, I had a lot of sex, I made some major breakthroughs in therapy, my father passed away, I developed a healthier relationship with alcohol, I helped a friend detox from drugs, and I started going to 12 Step meetings. The last few years have been incredibly difficult, but they’ve also forced me to grow. In the end, I don’t either Jeff or I reached the potential we each saw in the other. I am not the girl Jeff thought got away, and even if I was, he’s still just a great guy who isn’t ready for a relationship.

3. The same behavioral patterns emerge. I loathe the phrase “people never change.” What a cynical, depressing load of garbage. Of course people change. But unfortunately, a person’s internal evolution is not always reflected in their behavior. That’s the hard part. Jeff’s lack of successful dating experience in between rounds 1 and 2 was also cause for concern simply because he hadn’t put himself in many positions to have his behavior impact or be challenged by another person with needs and desires. When we started dating again, I could see that Jeff was more self aware. He was bolder and more adventurous. It was rad! The first month was amazing. We had so much fun. We connected. We had sex again, finally, and it wasn’t awkward or short! He had changed, I had changed, we had changed. Hooray!

Not so fast. About a month and a half in, we had a dumb misunderstanding — so dumb, that I can’t remember exactly what it was about, but it amounted to an “off” moment, nothing more, nothing less — that could have, should have, been nothing. In person, he immediately clammed up. Later, feeling concerned that he might still be festering over it, I emailed him a short note hoping to smooth things over, and, in a show of good faith and confidence in the intimacy and connection that had developed again between us, I made myself a little more vulnerable. But it was like a door had been shut and things were never the same after that.

Or, rather, they started to look the same as they had the first time around. Jeff began distancing himself in small ways, asking me to hang out during the day on the weekends, but finding excuses not to hang out at night, which meant we weren’t really having sex. He was still physically affectionate, but less so, and while I would tell him he looked hot or express admiration for his various talents, he would rarely return the sentiments. His texts and emails became almost entirely focused on a bunch of familiar complaints — disliking his job, not having energy at the end of the day, and, most importantly, feeling like he wasn’t “achieving.” His “stressors,” he called them. I was sympathetic, but I also had a raging case of deja vu.

I opted to just tell him that while I doubted it was his intention, his behavior was confusing me about his interest in me romantically and was hurting my feelings. Jeff, after all, had been my friend for years at this point, so while that kind of behavior in a relative stranger might have made me delete their number, I thought he deserved more respect than that. Besides, learning to acknowledge and articulate my needs, minimal though they may be, was something I had struggled with in previous relationships and I didn’t want to regress into old patterns either. I wanted to give Jeff an opportunity to explain himself, even if that meant being honest about how his feelings for me might have changed. Instead, Jeff saw this as a criticism, further exacerbating him not feeling “good” about himself. He went AWOL (yup, just like the first time) for a few days, emerging only to text me a short apology about not wanting to hurt me.  Aside from that brief back and forth, I haven’t heard from him since.

I actually have no regrets about dating Jeff again. We had some fun. It taught me that I need to be more mindful of not idealizing or falling for what I see as someone’s potential. It gave me a chance to articulate what I need and how I want to be treated, and that’s meaningful, regardless of the outcome.  Most of all, it confirmed what I always knew: people can change — I had, he had, we had — but that is not always enough.

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