Dealbreaker: He Had Low Self-Esteem

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“You must think he’s better looking than me,” Brian said, motioning to our waiter.

Brian started most conversations this way. I shifted my gaze and looked intently at my menu, pretending to study it, just to avoid continuing this conversation — a conversation I was no longer interested in having.

Brian was a guy I’d met leaving a party on a cold January night. He was cute and we exchanged numbers. We hung out a few days later, and thankfully he was just as appealing. Our conversations were entertaining. He got my offbeat sense of humor, and I admired his fierce loyalty to his family.

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At the beginning of our fourth date, the first 20 minutes of which were spent sitting in his car, he began inundating me with questions.

“How do I look?” he asked.

“Good,” I answered

“What about me looks good?” he went on.

“Ummm, I like your sneakers,” I said, not sure how to answer.

“What else, I mean about me looks good?” he pressed.

“You have a nice smile?” I guessed.

“No, I don’t! What else?”

The conversation went on this way. My responses were met with quick rebuttals and a request for further explanation about his “attractiveness.” By the time we got out of his car, I had run out of compliments and patience. But my rumbling stomach prevailed. Everyone has a day where they need to be told they’re special in excruciating detail while offering self-deprecating rebuttals, I thought. Chalking it up to him having an insecure moment, I agreed to another date.

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Our next date started out with more of his questions, but ended with amazing sex. The kind of sex that leaves your hair mussed and your skin glistening. Only seconds were spent in post-coital silence before Brian started in again.

“How was it?” he asked.

Amazing was the only word I had the energy to muster. I curled into him ready to slip into a blissful sex-induced coma.

“What about it was amazing?” he asked.

“Everything,” I said, hoping he would just let me fall asleep in his arms.

I tried hard not to engage, but he wouldn’t let it go.

“What do you mean by everything? You must have been with other guys who were bigger, more muscular, better at oral …why was I good?”

I kissed him on the lips hoping to shut him up and pretended to fall asleep, as he continued to whisper questions in my ear.

The next morning he seemed genuinely hurt by my incomplete answers; so much so that he barely spoke to me. As he was about to leave, he told me that he knew he wasn’t good in bed, and I didn’t have to lie.

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I tried to ignore him, but it’s in my nature to comfort people when they are upset. After a half hour spent trying to convince him that I did, in fact, think he was good in bed — and yes, his penis was a good size, and no, I hadn’t faked my orgasm — I was late for work.

We continued to date for a while, even though his constant need for validation and affirmation kept reappearing like a stray I had fed one too many times. I tried to pretend it didn’t exhaust me to have to stroke his ego and reaffirm his goodness on a daily basis. I had even come up with creative methods to beat him to the punch. I sent carefully crafted text messages, always beginning with “Hey handsome.” If I called him handsome, maybe he wouldn’t ask me why he was attractive, or what my favorite part of his face was. Some days it worked, and other days, no amount of affirmation-filled texts could keep the questions from coming. There were always questions. They came with us to dinner. They showed up at the movie theater. They even crawled into bed with us. The questions were the third person in our relationship.

“You must think he’s better looking than me,” he repeated, motioning once again to our waiter.

I looked up from my menu and caught that familiar gleam in his eye as he leaned closer, anticipating my answer. But it didn’t come. I couldn’t find the energy or the desire within me to placate him. I got up from the table.

“You’re a nice guy,” I told him. “You’re cute and funny. But you don’t believe that, and I am not the one who’s going to make you believe it. And I am not going to go insane trying to. I’m sorry.”

And just like that, it was over. I take responsibility for my part; I let it go on too long, gave in to his neediness too many times. A part of me genuinely thought that if I gave him enough praise, I could help build his self-esteem. But it was never going to be enough. When I realized my tears on the walk home were more from relief than from sadness, I knew I had done both of us a favor.

–By Kristol Roberts

This post was originally published on The Frisky.