A Date with the Twenty-Something People Pleaser

By: Destine Manson

"You don't owe them anything."

That's what my best friend told me over the phone when I contemplated going on a second date with a guy I was not that into. When it comes to dating, my first thought is always safety. My second thought is, embarrassingly, "what will they think of me if I say no." Whether it's just a second date or sex, I soon realized after having a couple of bad dates that I didn't know how to say the word "no" the way I assumed I did. With all the female empowerment around me and being raised by a father that spoke highly of strong women, I soon realized that being firm with men would only get more complicated the older I got. After leaving a date, I learned this lesson the hard way feeling like I failed myself and all the Megan Thee Stallion lyrics I swore I lived by.

The date started off rocky. Before I matched with this guy, every other date I went on was prefaced with days of texting back and forth before the actual date. However, despite having a dating app profile, I still preferred learning about a person face to face, so it didn't strike me as particularly weird when he didn't text me until the day of our date. We had not had an entire conversation at all prior.

I arrived on time. He was ten minutes late.

He was friendly and paid for everything, but I couldn't help but notice little things that bothered me. He stared at me for an extended period of time during the natural awkward silences that occur when you meet someone for the first time. I felt like he was looking at me more than he was really interested in what I had to say. I had never felt like that before on a date, but I had only been casually dating for a couple of months by then.

After we finished our food, he asked if I wanted to get a drink. I honestly did not plan on being out all night since I had plenty of work I had yet to finish. Yet, when he asked to get drinks after, I agreed out of fear of what it would look like if I said no. He repeatedly insisted that the bar and his place were just around the corner. He said I could do my work at his place on his laptop.

We had just met for the first time that day, and I didn't feel comfortable being in his apartment building alone yet. We never discussed expectations before. Honestly, I didn't know what mine were besides that I didn't want to have sex on the first date. I had been in a long-term relationship for four years and didn't know what casual dating looked like. My first mistake was saying yes to a drink when I knew I was yearning to get home to my desk and eventually my bed. I remember thinking to myself, "but he paid," and agreeing to walk to the bar with him in the brisk cold.

The bar he took me to was hidden behind a taco restaurant I frequently went to. When I saw the bar's ambiance, I perked up a bit. I was hopeful that maybe the night would end better than it started. We ordered our drinks and sat in a few more moments of silence. I tried my best to keep the conversation going. I wanted him to have a good time even though I was starting to run low on energy. We had already had drinks at the restaurant, and I was beginning to get concerned that I wouldn't be able to type the paper I needed to complete that night under the influence of alcohol. As we walked back, I kept saying how I needed to get my assignment done and couldn't come over.

"I mean, I live right here."

"Yeah, I know but maybe another night."

Did he not hear me the first time? The second time? He finally agreed to walk me back since our apartments were on the same street. We stopped at his door first.

"I had fun," I said. He tried again, reminding me that he would pay for an Uber back. I declined and told him that it was ok. I reached forward to hug him goodbye. Before I knew what was happening, I was trapped in the most uncomfortable kiss of my life. When I finally broke away, I immediately called my best friend to tell her how the date went. I told her how gross I felt. What could I have done differently?

I thought back to the advice that my best friend gave me after coming back from a less terrible date the week before.

"I don't know. Should I see him again even though I wasn't that into him?"

"I mean, you don't owe them anything."

I laughed when she said it, but at that moment I realized how right she was. Coming into adulthood, one of the first lessons you learn is how to represent yourself. In work spaces, classrooms, and making your own appointments, it's all about establishing your authority. We see adults do this all our lives.

I put down the typical walls I put up to come off as authoritative when I went on dates with men because I wanted to appear softer. He took advantage of that. He assumed I didn't know what I wanted. He assumed that because I stayed for drinks, I would do whatever he wanted that night despite my objections since the beginning of the evening. Not only is it essential to be clear about what you want to ensure you and your date are on the same page, but it could mean the difference between a great night and one you never want to remember again.

The next date I go on, I won't expect movie versions of strangers meeting for the first time. It shouldn't be up to women to remind others to respect us. However, some men in this world (especially in their 20s) have not yet grasped this concept of respect for women. Being in your 20s is a time of endless transition. Whatever point you end up at in that transition, you have to define yourself first before others do. Even if you're unsure, never let them see you sweat.