The guilt of dating

“Wretch. Don’t go! Don’t feel bad, you can totally back out.”

I had sat staring at that text from my friend Chum, knowing she was completely right. Everything in my gut was telling me not to go.

Yet I had found myself feeling guilty enough to end up at the Chili’s at the Legends outlet malls anyway, confronting three of my biggest nightmares: dating, outlet malls, and casual dining chains. The fact that this random dude had even suggested this as a date was a huge red flag for a girl who prefers local bistros and shopping online at Mod Cloth. It took everything in me to muster up the guts to go.

When I told her about the interaction that led to our date, Chum immediately knew what the problem was: I’m too nice. I had more or less been guilted into going on a date with this guy because he sent me a message in which he complimented my curly hair. I  then made the mistake of looking at his profile, which said he hated people who wouldn’t respond to messages; that a simple, “I’m not interested” would be best. So for three weeks, his comments haunted me until I finally just responded, “Thanks.” (I blame my Mom for making me so polite and not just ignoring the guy altogether.)

His message back was not only lightening-fast, but also fairly snotty: Finally responding after three weeks? Nice. LOL.

LOL? I should have ignored him then. However, things escalated quickly — way beyond my control. It was because I felt the need to apologetically retort. Which calmed him down. And then that made me feel bad and I continued a conversation with him. And eventually, this growing guilt turned into a lunch date at a restaurant I hate with all of my being.

Which is how I found myself sitting on a park bench in front of Chili’s, waiting on somebody I knew I would have no interest in dating.

My gut told me to run away before he showed up. And then again when he arrived, particularly because when arrived — 10 minutes late — he commented on how fancy I looked in my $25 cotton maxi dress from Target. It was the most comfortable thing I owned.

We sat down to eat and I scoured the menu for vegetarian options. As suspected, appetizers are about the only options for me in casual dining purgatory, so when he ordered a burger, and I got a margherita flat bread appetizer, he pried.

“I’m a vegetarian, it’s the only thing I can eat on the menu,” I said.

“Oh, I love meat,” he said. “I hope that doesn’t ruin things for our future.”

I cringed and thought, “Eat all the meat you want, buddy. We have no future.”

We made small talk as he fumbled with his phone, frequently texting random people and commenting on how busy he is because he owns a construction company and has three boys. He blandly talked about building giant houses. I tried to make small talk, mentioning the days I spent advertising for home builders and communities in North Carolina. It was one of the hardest conversations I have ever had.

I told him about writing and roller derby. I explained that I have no free time due to practices and traveling for games. I hoped maybe he would get the hint.

The date seemed to go on for eternity, until finally, it was time for him to get back to work. I offered to pay for my app. But he insisted he’d pay. As he signed his name to the receipt, he closed the bill folder triumphantly and said, “Well, our first date is in the books!”

We walked outside and I hurriedly thanked him. We said our goodbyes and was happy to realize I had never given him my phone number.

As I backed out of the Chili’s parking lot and headed home, my phone began to ping with dating app messages. I waited a day before I checked them and saw, “Hi. I’m sorry I was so nervous. You were just so smart and pretty that I couldn’t help but get nervous.”

He asked for a second date. And rather than feel guilty, I deleted the app and never looked back.

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