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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Alex Wise served over 5 years as relationship expert helping women from around the world figure out the men in their love lives from an honest, male perspective. Alex is one of the contributors and editors for dating website. He is passionate about thought leadership writing, and regularly contributes to various career, social media, public relations, branding, and online dating communities.


  1. I need help Please!! I have been dating a girl for 3 yrs and it has been totally awesome, we have even talked about marriage, but she seems to have cooled off and my present status is broke up. She told me that she just wants to be friends right now with the possibility of getting back together in the future, although she says she still loves me, and I love her. Before we broke up I introduced her to a business contact acquaintance of mine to help her better her business. The next thing I know she gives him free tickets to a concert she is going to, they are texting, emailing, talking on the phone, and have been to lunch together while we were still in boyfriend/girlfriend status. I agree to try to be just her friend, nothing much has changed, we still would go out alone, go to the beach, etc, except there was to be no physical contact between us, just maybe a hug at departure, and her not saying she loves me when we depart any more, even though she said she did love me. On another occasion I take her to a marina bar in my boat, some starving artist there unbeknown to us sees her with me and sketches her nude on a napkin and gives it to me. I thank him and give it to her, he was nice about it and we both are not mad. He signed his last name on the napkin. The next thing I know she researches his name, finds his email and sends him an email thanking him for the sketch. I did the same thing because it seemed harmless. But then they begin emailing back and forth, and he invites her and I back to the marina bar to listen to some live music which is also where he works as a part time bar tender I take her there and they meet in person for the first time she is very friendly with him, shows very positive body language, touches him several times on the arm, play punched him, and rubbed his head once, and they hugged two or three times, all of this right in front of me. To interject, I have told her prior to both of these situations that something that I have a severe hatred for is to be in a relationship with a girl and she starts up a relationship with someone I introduce her to, or that she meets while she is with me. I make it very clear to her that I personally feel it is the worst thing that someone can do to a bf/gf/mate, etc, that they supposedly love. So as I ask her directly and she tells me that she has been with the business associate to lunch one time, and the starving artist as well. And these have also have been non business lunch dates, since the business associate tried but could not be of any assistance to her in her business, nor of course the starving artist/part time bartender. She has volunteered very little information about having contact with these two individuals, even when we were in a bf/gf relationship, not sharing texts, or emails, just telling me the gist of them, but appears to be honest and answers my direct questions about them. As I see what I feel is a relationship developing with both of the people I have introduced her to, I begin to feel like she is using me to meet guys, since both times that I have introduced her to someone or she has met someone when we are going out, she has began a progressive friendship/relationship with them, and I reminded her of what I said about how I feel about her going after guys that I have introduced her to, I ask her to break it off with these two with unless it was business related or I cannot even remain at friend status with her because it is so disgusting to me, and virtually gave her an ultimatum and drew a line in the sand. Let me interject this she has at least 4 other guys that she is texting, emailing, and/or goes to lunch with and/or out for drinks with, she got drunk with one of them and had to spend the night at his house alone in the pinnacle of our relationship and swore they did not have sex or intimate contact. I told her that I did not care if she continued pursuing the guys that she met or knew on her own period, or any guy she may meet in the future, just the two she met through me. She told me she could not do that and chose those two guys that she hardly even knows right now over our friendship. I told her the door is always open if she should change her mind, as long as in the interim that she didnt get into a bf/gf relationship with the two, or have a sexual relationship with anyone else, and if that should happen, dont worry about calling me. My question is, am I wrong for giving her an ultimatum, if so how? What could I have done different? Please Help, Wildriverdude

  2. Dude there is an old saying my grandma use to say when I was dating…”do not take a candle to see at night what you can plainly see during the day”. In other words, it’s right in front of your face. This girl is either playing the field or more interested in building her business than a relationship with you. One word of advice “run”…

  3. I’m not gona write a big essay telling you what to do with your life…Long story short, if your girl is constantly going out with other guys while you are dating her, she’s basicaly a wh— (i’m sure u can make out the rest of that last word) and apperantly doesn’t return the same deep feelings that you have for her (AND i mean GOING OUT..). It happens. On the other hand, if this’s happening and your not in dating status, then you shouldnt be complaining cause you can do the same… Conclusion, if she’s doing the whole going out with guys while you are in dating status with her and you have told her before you are getting annoyed, time to find a new girl friend then. Cause she apperantly doesnt feel the same about you or she’s one of those girls that cant stick to one guy. Plenty of fish in the sea. You’d be surprised, you may not believe it but when you find that new girl, she maybe more special than you ever thought this current girl is. She’ll prolly make you feel like the whole world to her or something. (GOOD LUCK AND HOPE YOU FEEL BETTER =)