Ben Higgins on The Bachelor Winter Games

The MW Team Reveals Our Worst Dating Mistakes

Riley’s dating tell-all was such a success we decided to spill the details on all of the MW contributors’ biggest dating errors. Before we share, can we agree that everyone deals with things differently, and most people don’t set out to hurt others?

Hindsight truly is 20/20, and it’s never more clear than when you’re getting to know someone outside your comfort zone. We also know this doesn’t make breakups hurt any less. Anyway, here’s what the guys had to say:

While living in Ohio, a girl asked me on a date. To avoid hurting her feelings, I told her I was going to be in Detroit for the weekend (five hours away). She knew where my apartment was, and I feared she would stop by, so I did in fact plan a last-minute trip to Detroit that weekend. In retrospect, it may have been easier to just say no.  — Jordan

Do not take a road trip with someone you’ve only been on a few dates with. A few years ago, I was dating someone, and we decided to go on a 10-hour road trip. After a few hours in the car I realized I was not as excited about this relationship as I thought — and we were a long way from home. I shut down, my date recognized this, and the final five hours were silent. When we got to our destination I decided it was best I fly home immediately.  — Ben

One of my favorite movies is Just Friends with Ryan Reynolds. In the movie he advises not to go on “day dates.” Well, I broke this rule in college and took a girl out to lunch. I thought we were connecting, but later I heard she was dating someone else and she didn’t think we had gone on a date. I learned my lesson: Be intentional about making it clear when you’re interested.  — Mitch

Instead of being honest with someone I knew wasn’t a long-term partner, I continued the relationship because I was scared of hurting her feelings. All I did was end up hurting her more later on. If you’re not feeling it on the first couple dates it’s better to shoot them straight and avoid more disappointment later.  — Brandon

While casually dating a girl, I began looking for a way out. I became a jerk in hopes she would end things. Instead, she asked me to dinner with her family. I agreed and a couple of hours before dinner, I told her I couldn’t make it. She called things off the next day. Perfect — that was the plan. In reality, doing what I did was way worse than being honest and respectful.  — Dylan

What’s the hardest dating lesson you’ve learned?

Image courtesy of ABC/Lorenzo Bevilaqua

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  • Reply
    Lourdes García Morán
    April 2, 2018 at 6:15 pm

    I laughed and learned from your mistakes you should make a publication of Worst Dating Mistakes but from the perspective of girls. Hi from Honduras.

  • Reply
    April 3, 2018 at 7:49 am

    I really appreciate these lessons being shared. Honesty, has been the biggest lesson I’ve learned. I’m a very empathetic person, which feels like a curse sometimes but if you are not feeling it anymore, it’s okay. No matter how little or how long you’ve been dating the person. Everyone will survive and learn something from the experience. Not being upfront with someone because you do not want to hurt their feelings is just prolonging the healing process. They will respect you being honest later down the road, if not immediately. And that bridge will have not been burned. <3

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