“How I’d Handle A Dating Do-Over”

What would you do differently if you had a second shot with the one that got away? Find out what made these daters wish for a “dating do-over” — and what experts have to say about their romantic regrets.

By Ronnie Koenig

hen it comes to dating, don’t you wish there was a time machine that could take you back to fix the mistakes that may have ruined a perfectly good relationship? Read on to learn what these daters would change if they got a chance to redeem themselves romantically.

Dating do-over #1: “I wouldn’t have accused her of cheating on me.”
Tom*, 33, met a woman he really clicked with online and the two of them went on several dates together. “I felt we were about to become an actual
If she smiled at a waiter, I accused her of flirting.
couple, and maybe that’s what scared me,” he says. “I started seeing things that I now realize just weren’t there. If she smiled at a waiter, I accused her of flirting. When I walked into her apartment building and saw her chatting with her neighbor — who happens to be a good-looking guy — I’m embarrassed to say that I accused her of sleeping with him.” Tom thinks that his parents splitting up when he was a teen due to extramarital affairs was present in his thoughts when he made the cheating accusation. “I have to learn how to separate their story from my own,” he reflects.

The expert’s take: “Tom sabotaged his budding relationship because his parents’ affairs and subsequent divorce made him frightened of making an intimate commitment that might end with the same heartbreak he saw them suffer through,” says Carole Lieberman, M.D., psychiatrist and author of Bad Girls: Why Men Love Them & How Good Girls Can Learn Their Secrets. “By accusing this woman of flirting and sleeping with other men, Tom insulted her — and it frightened her off.”

Dating do-over #2: “I would have been more flexible and open to new experiences.”
Jimmy, 55, has been living the bachelor life for as long as he can remember. “I’ve had many relationships with women, but I’m used to doing things my way,” he explains. So when friends set him up on a date with a young musician, he found himself laying out some rules for her. “I don’t go see those types of movies; I don’t like that type of food. I think she got the idea that I wasn’t willing to try anything new,” Jimmy recalls. “She probably saw me as an old fart!”

The expert’s take: “Jimmy is not a 55-year-old bachelor by coincidence,” says Lieberman. “Faced with dating a young, vibrant woman, he felt out of his league — and out of control. So to try to protect himself from impending heartbreak, he set up these rules which ultimately brought about the self-fulfilling prophecy of her seeing him the same way that Jimmy saw himself — as an old fart.”

Dating do-over #3: “I would have told him that children were a priority for me.”
“People always say to never bring up marriage and babies when you’re first starting to date someone,” says Cadence, 38. “But I went too far in the other direction. I was so scared of scaring this guy away that we ended up on completely different pages. I could have saved us both a lot of time and heartache if I made it clear from the get-go that I wanted to have children — and soon!”

The expert’s take: “Cadence was self-conscious of her biological clock ticking so loudly that the whole world would hear it and be frightened by her desperation to have babies,” says Lieberman. “Fearing that this would turn men off, Cadence overreacted by denying her true feelings. Because she was so obsessed with finding someone to marry and have babies with before time ran out, she inadvertently pushed some potential partners away.”

Dating do-over #4: “I would have lightened up and seen the glass as half-full more often.”
“I’m not the most lighthearted guy to begin with, but when I met E., I was definitely in a funk,” says Sebastian, 41. His constant whining and complaining “about everything from
I was too nervous about being rejected.
my career path to the weather” was a big downer for E, his new love interest. “She was probably right to run in the opposite direction. If I had another chance with her, I’d fake it ‘til I made it — I’d smile for no reason, watch funny movies and try not to take the little bumps in the road quite so hard,” says Sebastian.

The expert’s take: “Sebastian has an intense personality that culminates at times in both a melancholy demeanor and a critical voice,” says Dr. Stephanie Knarr, a marriage and family therapist practicing in Washington D.C. “It is possible that this may come from a difficult childhood, an alcoholic parent or a mood disorder; however, it’s a big turn-off to be regularly negative and critical while you’re dating — or during a marriage, for that matter! A successful, healthy partner is going to generally have a positive outlook most of the time, and that type of person usually wants to date and be matched up with people who are likewise optimistic and non-judgmental.”

Dating do-over #5: “I would’ve tried harder to be physically affectionate with him.”
June, 36, regrets letting her sexual hang-ups get in the way of a staying with a man who could have been The One. “I wasn’t willing to make it a central part of our relationship. I thought that being good friends was enough. My boyfriend at the time wanted to please me, but I don’t think he could have,” she recalls. “It kills me that this man is out there right now, being someone else’s husband — and he is; I looked him up!”

The expert’s take: “June has difficulty making herself vulnerable when it comes to flirting, physical affection and sexual intimacy,” says Knarr. “Any of these hang-ups are going to make it unlikely for a relationship to blossom into a long-term romance with a healthy partner. Since June unfortunately thought that being good friends was going to be enough for this man, she would likely benefit from gaining some additional knowledge about healthy intimacy in loving relationships and resolving any previously learned unhealthy intimacy patterns before seeking out a new romantic partner.”

Dating do-over #6: “I should have kissed her when I had the chance!”
“Why didn’t I just kiss her?” Robert, 46, laments. All signs said she was ready and willing, but the self-described “serial dater” just couldn’t pull it together with this woman. “I was too nervous about being rejected. Hindsight is 20/20, but even then all of my friends were telling me that this woman was into me. Who knows why I thought she was too good for me; she probably was! But I still want her back.”

The expert’s take: “Robert is struggling with his self-esteem and sabotaging the dating process by not sticking his neck out and taking a risk when he needs to,” says Knarr. “Robert would likely benefit from learning his own worth in a relationship by performing a thorough evaluation of what qualities he has to offer a future partner. A healthy dating experience is based upon having done the personal work of knowing exactly which qualities one has to offer in a relationship — then, any dating rejections are much easier to cope with, because they are not about an individual’s self-worth; rather, they are simply about having a lack of compatibility with another person.”

*All names have been changed to protect the contributors’ privacy.

Ronnie Koenig is a freelance writer based in Brooklyn. Visit her online at
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