Trying It Again With Bob

Wednesday | July 13, 2016

Love Letters Dating

Trying It Again With Bob

Dear Love Letters,

After ending a serious four-year relationship with a guy, I found myself ready to get back into the dating world, or so I thought. I started dating one guy, “Bob,” from an online dating app, then met another fellow offline and subsequently broke it off with Bob because I thought I liked the second guy more. Bob and I weren’t exclusive and had just been in the early dating stages. I didn’t end up with either of them, and went on to be single for the next few years.

It was a bumpy few years, and now I am 33. Recently, I’ve actually reconnected with Bob through digital serendipity (I swiped right!). We’ve been seeing one another here and there, nice and slow. I really like him but I am concerned, however, about hurting him again if things fizzle out. While I have grown so much, I find myself questioning whether I have grown enough to really get back into a relationship. I feel ready, but maybe a part of me looks back at the four years I was with someone in my mid 20s and sees only a waste of time. You see, that person I was with for four years was NOT my match at all, and I was too young and didn’t know myself enough to understand that it’s OK to express what I want and accept that it wasn’t him. I stayed with the first guy too long, knowing deep down he wasn’t for me. Now I find myself asking if Bob is really for me. Am I just scared of spending the time on figuring that out? How do I avoid a repeat of history?

– Repeating History?

There is no repeating history here. Every dating experience is different, every right swipe has its own potential. You’re older and wiser now, and Bob has nothing to do with your former relationship. (Say that out loud a few times, please. “Bob has nothing to do with my former relationship.”)

The only possible pattern I notice here is that you like to bail on Bob before you have answers. In Round 1, you dumped him before there was exclusivity. Now you’re thinking about dropping him even though you’ve barely spent any time with him. Shouldn’t you give yourself some time to get to know him again? Shouldn’t you enjoy the serendipity for a few months before you ask big questions?

Dating takes time, and you can’t go into every experience questioning whether it’s worth the risk. If a relationship fails, it doesn’t always mean you wasted your time. It might just mean you had an experience and a lesson was learned.

– Meredith

Readers? Bob? Repeating History?

Dating

Featured Comment

Labeling a wide swathe of time in your life as ‘a waste’ is not useful in any way. It’s done now. You recognize that it wasn’t the relationship that you were unhappy with – it was your own choice to stay despite not feeling things were ‘right’ that was the issue. Good. You’ve gotten your takeaways – now move past this. You need to learn to trust yourself a little. That was the issue in the first place.

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