Love in Hindsight — When Should You Go Back for a Do-Over?

Love in Hindsight — When Should You Go Back for a Do-Over?

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Here’s how it typically works:

1) I’m in a bit of a romantic rut.

2) I happen to see a name on my phone or email contacts or just randomly recall a face in the old mind’s eye. This is typically someone I went out with, eventually slow-faded, and figured I’d never think about again.

3) I am stricken with doubts. Did I do the wrong thing when I told her I was moving to western Nebraska to start subsistence farming? And hold up, why did I dump her again? I honestly can’t remember! Who do I think I am dismissing perfectly non-defective women, Henry VIII???

4) I begin to romanticize this near-forgotten girl and dismiss the vague memory of her telling me an endless story about her sister’s hair-care line and what I’m fairly certain are some seriously unforgivable choices in reality television.

And just like that, I’ve convinced myself I made a terrible mistake.

Admit it: You’ve done this too — suddenly gotten the Hindsight Hots for a person whom you once lied to about having parvo so you didn’t have to see “STOMP” with him.

But we’re always reading wedding announcements (shut up) about married couples who (shut up) fell in love after an unsuccessful first go-around. So, let’s do a little investigative work and break this down. Hopefully we can see when it is and is not the right move to contact your potential hindsight soul mate again.

“CSI: This Old-Ass Relationship You Might Want to Try Again”

The first thing to remind yourself of is why you gave this person walking papers in the first place. (If he gave YOU walking papers, then stop even considering contacting him. Just don’t. Let him go. He is still very, very sick with parvo.)

This is typically a problem for me because there’s actually nothing wrong with most of the girls I date. Usually, I just didn’t “feel it,” so I bailed. The problem with this type of reasoning is that it’s childish and ephemeral. After a few months I can’t really remember what was so wrong with the chemistry, just that the girl was pretty and sweet and drank beers with me while smelling like flowers. Then I get The Regrets, and I start inching toward my phone or computer, thinking that one little text or email wouldn’t kill me.

But, there are other times when there IS something specific — the girl who didn’t know the difference between “their” and “there,” or the one who had this weird habit of squeezing my shoulders super-tight when we made out like she were afraid I was going to fly away, or the one who did improv comedy. Sometimes I have to remember that as pretty and nice and good-smelling as some of these women were, I did have a clear reason for peacin’ out.

Go Over the Timeline

Also important: How long did you date this person? Was it a once or twice thing, where you can barely recall anything about him save for the recollection that he itemized the dinner bill like a coked-up CPA? Or did you date for a few months before deciding that somebody who gave you acid reflux wasn’t your destiny?

I’m always ending things early, which means I have a lot of numbers in my phone of women I barely know who become really, really intriguing to me after a few glasses of wine or long periods of sexual dormancy. So, it’s easy for me to take a girl whom I was sort of bored with by date three and recast her in hindsight as Sofia Vergara when I’m feeling lonely and undersexed.

But with longer relationships which just kind of faded or fell apart by your hand — you’d better be sure you want to go back to it, because you were Over It once before and you might be still. Don’t dredge some poor dude up from the bottom of Lake Breakupeechobee only to cruelly throw him back like an legally undersized mullet.

Ask the Tough Questions

Ironically, so as not to be selfish, you have to do a little navel gazing first. Why are you feeling this way? Are you in a bit of a dry spell? Anne Hathaway movie spree? Just want to remember what it’s like to have someone else’s hands on your butt in front of a roaring fire?

Let me say this: I think there’s often a good reason to go back and give things a second go, especially if something made you dismissive of somebody for the wrong reasons. Maybe you were getting over a breakup, or busy with a new job, or convinced that you couldn’t find love with somebody who wasn’t ALSO a Unitarian Universalist (although they’re notoriously inclusive, so that doesn’t make much sense).

If you’re feeling a sudden gravitational desire to make that call and it’s not based on your loneliness or horniness or narcissism, then you have to ask yourself the next tough question: Does this person want to hear from you?

Because this isn’t all about us, is it? We did the dumping, and now we want to march back into somebody’s life as if nothing had happened. It’s going to take a level of humility, which requires some courage, to make this call or send this email.

Finally, Make (or Don’t Make) the Call

So, you make contact. But remember: Being dumped or slow-faded sucks. Chances are, this person is either going to ignore you. You know, “[Redacted]? Ha ha, nice try. Call me again never, you no-calling, gastrointestinal-virus-faking a-hole.”

But! If this was a situation where the person seemed genuinely disappointed that things were over (often indicated by a “Hey, what happened, I thought things were going great?” text or email), you may have a shot.

If you really think this guy was bummed that you ended it AND that he’d be amenable to hearing from you again, you have to realize what you’re doing. That is, putting yourself out there to someone who might take you up on it — and who might be really happy that you’re giving it a second shot … or who might be really happy to go “Count of Monte Cristo” on you.

And, finally, be prepared for the worst scenario (this one happened to me): Your hindsight dumpee accepts your invitation to go out again, and you end up in the dreaded Double Dump scenario. When we went out the second time around, I remembered exactly why I wasn’t into her. I quickly realized, horribly, that I now had to vaporize on her all over again.

Look, there are very few absolutes in life. Who can say that you SHOULDN’T actually give a second shot to that quiet guy whose only crime was never having seen the Michael Keaton “Batman.” Maybe you were just in a weird place at the time — or maybe after a second try, something will click.

It can happen, though it’s rare. But anything that’s worth it usually is.

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Love in Hindsight — When Should You Go Back for a Do-Over?

time to read: 5 min