“I Messed Up, But I Fixed It”

Whether it’s first-date nerves or ending a budding relationship too soon, these guys made some regrettable mistakes with women. Here’s how they made things right again — and you can, too.

By Dave Singleton

t happens to all of us at some point. We mess up — big time. Maybe you had an awkward first date that should have gone better, sent a text meant for another woman — or worse, you acted impulsively and broke up with her too soon. There were hurt feelings, doors slammed, and it looked like your, says that
Make your case and hope for the best.
romance was DOA. F. Scott Fitzgerald once famously said, “There are no second acts in American lives.” But does that hold true when it comes to dating?

Sometimes you fail at dating, and there’s nothing you can do to fix the problem. It’s a hard lesson; but occasionally, those rare second chances do come along — if fate allows and you play your cards right, that is. Recently, I spoke with five guys who blew it with their romances, but managed to reclaim their honeys’ hearts in the end. Their mistakes were only the first acts of their stories; how they fixed them is the satisfying conclusion. Read on…

“I accidentally sent her a text meant for another woman I was seeing”
“I’d dated Marcie for two months before the ‘text bomb’ (as I like to call it) went off,” said New Jersey native Keith, 29. “One night I was out with my buddies, met a woman, we flirted a bit, and then I texted her afterwards — including one message that was a little racy. But I accidentally sent the intended for her to Marcie instead! We were not exclusive yet, so I wasn’t technically cheating, but it was pretty bad. Annoyed, Marcie texted me back immediately and basically told me to buzz off. I really did like Marcie, so I apologized to her profusely over the course of the next two days. I sent flowers; I went to her house. Once Marcie got over her initial anger and heard from me — face-to-face, which was important — that I wanted to move forward with her, our relationship got back on the right track.”

Lesson learned: In our high-tech world, mistakes — like a misdirected text or email — are bound to happen at some point. A flub like this often creates a delimiting line in the sand in a couple’s relationship. Couples can either retreat from it and break up, or take it as a sign that expanded communication and commitment is necessary to move things forward. If you want to save your budding relationship, don’t ignore the elephant in the room when it comes in the form of a misdirected text, email or IM. Were you being impulsive, but now regret it? Make your case and hope for the best. Even though you technically might have done nothing wrong, when someone’s feelings are involved, logic usually goes out the window.

“I was nervous, so the conversation during our first date felt super-awkward”
“I met Tina through an online dating site and we talked on the phone for a week,” says Maryland resident Jeremy, 28. “Our conversations were fun, upbeat and easy. I asked her to dinner, but when I met her at the restaurant, I suddenly became tongue-tied. She was much better-looking than her photos. It’d been so easy to talk to her on the phone, but in person, I sounded like a dolt. The date ended with an awkward goodbye. I was so frustrated! This just didn’t seem right. I debated letting it all go, but the next day, I called her up and basically asked her to please forget everything I said to her the night before. I told her I’d had an off night and that after some great phone conversations, we owed it to each other to give it another shot. The next night, we went out again on a ‘do-over’ date. I made light of the awkwardness and acted like this one was our ‘official’ first date. We have been seeing each other ever since then.”

Lesson learned: Being upfront and making light of a gaffe is the best course of action after an awkward encounter and want a second chance, since a sense of humor is often the antidote to such issues. Be courageous enough to speak up and admit you want the opportunity to try again with your date. Next time, remember how counterproductive nervousness is and just try to behave like you normally would. It’s actually quite liberating to realize that working too hard to get something you want can actually have the opposite effect. The person you’re trying to dazzle would be more impressed if she didn’t feel overwhelmed and instead got to know the real you. Of course, if your date doesn’t want to give you another chance, it’s best to just let it go. She might have had her own reasons for not connecting with you romantically, so move on to the next prospect. Take the lesson you learned this time into making your next first date a better experience.

“I didn’t give her enough space to get over her previous relationship first”
“I had recently gotten out of a bad 20-year marriage and felt like a kid in a candy store,” says North Carolina native Thomas, 44. “I dated numerous women in my first year of being separated, and that had plenty of exciting moments (as well as some frustrations). But then I met a lady who
I could tell that my girlfriend was ready for more, but I wasn’t sure what I really wanted.
knocked my socks off — and she was also a recent divorcée. She made it clear to me that she was new to dating and wanted to take things slowly. I agreed that it was a great idea, but I just couldn’t do it. I wanted to see her all the time, and I think she thought I was relentless in my pursuit. After five months, she broke up with me, crying and saying that she felt too much pressure. That’s when I realized that I really needed to pay attention to what she was saying — it wasn’t that she didn’t like me; she just needed more space. So I told her that we could figure things out later and I backed off. Instead of having daily interactions, now we see each other a couple of times a week. Having a bit of space actually really works well for me, too. I’m not sure why I pushed so hard to get so serious with her so quickly, but I was able to adjust my approach to a slower, more realistic pace and we’ve gotten along swimmingly ever since.”

Lesson learned: There’s a really important point here, especially for older daters that are on a different track than their younger counterparts: timing matters. At midlife, dating often involves juggling more responsibilities (kids, jobs, mortgages), longer transitions between relationships (you’re newly single after years of being coupled up), and deeper entanglements (separation and divorce can take a long time and be costly). So there are legitimate reasons for someone needing additional space, which can benefit both of you because it allows more time for mutual attractions to bloom organically. Recognize that infringements on another person’s personal space can often be a sign of insecurity or loneliness, which are issues you need to address separately from your dating life.

“I broke up with her instead of taking things to the next level, then regretted it”
“After six months, we got to that make-or-break point,” recalls Virginian Sean, 34. “I could tell that my girlfriend was ready for more, but I wasn’t sure what I really wanted. So, I bailed and distanced myself from her. She ended up confronting me about being emotionally unavailable, and we broke up. I knew about two weeks later that I’d made a huge mistake. I wrote my ex an apologetic email and told her that I wanted to see her again. She replied and said she’d think about it. We exchanged emails back and forth for a week, which was a good thing for us. We talked a lot in those emails about the kind of relationship we wanted and what would be different if we were reunited. Then, we met up and worked things out together in person.”

Lesson learned: In this case, an apology (and some well-written communications) served as the kindling that helped reignite the fire in Sean’s relationship. Things don’t always turn out that way, but if there’s any chance to recover after prematurely pulling the trigger on an iffy relationship, it’s up to each of you to accept a share of the responsibility and then say what will be different going forward to make both partners happy.

“I put up a wall instead of communicating with her about why I was so unhappy”
“I was stressed both at work and at home with my kids,” says Massachusetts native Ted, 42. “I share custody with my ex of our two children. Ten months into my new relationship with Allison (who also happens to be divorced with two kids), we moved in together. Soon after that, my stress levels got so bad that I stopped talking to anyone and retreated into my shell. Allison tried to break it, but there was no getting through to me. After a few months of this behavior, she snapped and said that she felt like she might as well be single again. Allison left home for a week, which gave me time to think about why I was shutting her out. After taking some time to cool down, dealing with it was pretty simple, and we managed to work out a compromise. I told Allison that I’d do what I could to be more communicative about my problems if she’d stop taking the times I withdrew from her so personally.”

Lesson learned: Speak up when stress overwhelms you, or you’ll risk having a good relationship going south prematurely. It doesn’t mean that you’re the one who has to do all the compromising, either. In Ted’s case, the solution was to open up a dialogue so at least there was some room for negotiation on how they’d try to deal with it in the future.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Visit his website, follow him on Twitter, or email him.
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