6 Valuable Lessons Learned From Dating Mr. Wrong

When it comes to pretty boys … don't. Just, don't.

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We've all had some horrible first dates. But what about terrible relationships? If you're feeling alone in your quest to find "Mr. Right," take a look at some lessons that our readers have learned from "Mr. Never (Ever) Again."

Now, an ode to all of the losers that we've dated and the key takeaways from these mistakes:

1. Mr. Big Spender
Beware of the guy that overdoes the "grand gesture." While sure, a dozen roses make most women swoon … several dozen? Seems like overkill.


Single mother Shari began to notice a pattern developing in her relationship with her fiancé last year. After the two met on Match, she quickly fell in love with his extravagance. "The whole time we were together he was always doing things in such abundance," she said. "If he sent flowers, he sent six dozen, if he gave me a bag it was a Louis Vuitton." Soon enough, she realized that what he overcompensated for materialistically, he lacked emotionally. 

"As soon as he presented the ring, it was as if he owned me," Shari said, "and when he messed up, he just bought me more things, but none of them were enough to keep me happy." She broke things off shortly after, and plans on taking her time before settling down with someone again.


Lesson learned? If your man tends to show off, make sure he isn't doing it to distract you from his true (and in Shari's case, possessive) colors.

2. Mr. "You've Got This One, Right?"
While yes, it's the 21st century and there's nothing wrong with going Dutch on your dinner bill, there is definitely something to be said about the commitment level (or lack there of) of a guy who can't step up and treat you every once in a while. Kim spent three years dating someone that she now describes as "the cheapest guy on the planet."  

"When it came to dinner dates, movie tickets, you name it, I paid for it. Occasionally we would split it, but that was rare too," she said. Last year on the Fourth of July, Kim realized that she would never be happy settling for a freeloader. "I bought us tickets to the Yankee game, even though I had been upset for weeks prior about how cheap he was all the time," Kim said.  "On the day of the game, I was miserable, because I paid for everything — surprise, surprise. I came home crying, only for my Mom to tell me that she slipped him $50 that morning and told him to 'Take care of me for the day'." [Yes, you read that correctly. Kim's ex pocketed her mother's sympathy money.]

Lesson learned?  "Never date anyone who's cheap — it's literally the most unattractive quality a person can have."


3. Mr. Too Much Too Soon
You know those instantaneous butterfly feelings that grow in the pit of your stomach when that person walks into the room? Well, Jordyn dishes on why you shouldn't let them override your common sense.

"I dated Ben through my job. We had become really close friends, and since we worked 80-hour weeks, we spent virtually no time with anyone aside from the people we worked with," Jordyn said. Soon long office hours turned into post-office drinks and the two began texting on the reg when they weren't at work. "We instantly became permanent fixtures in each other's lives in the matter of a few weeks, and our relationship escalated as quickly as our friendship did," she continued. "We were seriously dating and keeping it a secret from all of our co-workers, and he dropped the L-bomb only a couple of weeks later." The two met each other's parents and spent long weekends together, only for the relationship to fizzle out as fast as it started, when they realized that they hardly even knew each other.

Lesson learned? Consider your relationship your biggest investment. Would you drop all of your savings into a stock that you haven't thoroughly researched? Probably not. Your heart is a prize, and you want to make sure that whoever wins it, is worth it. 

4. Mr. Pen Pal
You know this guy. He's funny, charming, and an all around catch … according to your IPhone. James fills us in on how a virtual relationship doesn't always translate into the real deal. 


James met Joseph on a dating app, and was thrilled to find that he liked him even more when they finally met in person. Drinks turned into a four-hour dinner and dinner turned into a walk through the park. "We went on three or four great dates, but while the texts were still coming in, the dates were falling through." Every time that James brought up going out again, Joseph became distant and vague, always steering the conversation away from any actual plans. James's frustration began to escalate because he didn't see the point of constant communication with zero delivery. "We would text all day, every day. At first I enjoyed the attention," he said, "but after weeks of not seeing each other, I grew tired and bored." Eventually, the texts grew fewer and farther in between, and James's coworkers got tired of trying to decipher the meaning behind every received emoji. "After three weeks of incessant texting, I finally gave up," James said. 

Lesson learned? Be wary of the allusive texter — odds are, he won't measure up in real life. 

5. Mr. Party Animal

He loves you, but he loves the club scene more. It's not you, it's him … until he wants one more chance, and Samantha shares exactly why you shouldn't give it to him. 


Samantha's ex boyfriend was sweet and genuine … until it came to the weekends, when he became frustrating and MIA. As a Columbia law student, she found keeping up with his partying lifestyle to be exhausting, but also didn't want to keep him from having a good time. "He wasn't cheating on me at clubs, or putting our relationship at risk in that way," she said, "but I still didn't feel the sense of companionship that I was looking for in a partner, it was like I was constantly babysitting him." When it became clear that his weekend plans with his friends would always win out over showing up for her, Samantha realized she wasn't going to change him, and that despite years of dating, it was time to let him go to grow up on his own. 

Lesson learned? "If he goes to more clubs and electronic dance shows than family functions and dinner dates, kick him to the curb and find yourself a real man."

6. Mr. Pretty Boy
This unfortunate lesson comes from yours truly. I had to learn the hard way that when a dude loves his shoe collection almost as much as he loves his own reflection, he's not likely to make room for you anytime soon. I repeat: pretty boys will always care about themselves more than they care about you.


Their hair! It's so perfectly side-swept! And their loafers? Always polished and perfectly laced. Their hearts? Pretty much off-limits. But you've got to admit, there's nothing sexier than a confident guy who has his life together … until you realize that it's all a façade. Each attempt to dig deeper than his wardrobe left me coming up empty handed. Now don’t get me wrong, I'm not saying that every nice-dresser is shallow, however, if they take more pride in their appearance and status than they do in your relationship, you might as well let him take his watch out to dinner … even if it is a Movado.

Lesson learned: When it comes to pretty boys … don't. Just, don't.

What have you learned from bad boyfriends? Tell us in the comments below.