Don’t Make This Mistake When Dating Multiple People

The lesson I learned last night.

It’s almost 1 am. I got back from going on two dates, in a row, with two different people.

I dazzled. They adored me. I turned them on. They both wrote back immediately after about how much fun they had.

And yet, mistakes were made.

By me.

For a few months, I dated Sean and Marc. However, both of them suck balls at communication. I don’t need constant messaging (although it would be nice on occasion) but going days on end not hearing from either of them pissed me off.

I decided I was done with both of them.

And right when I decided I was done and went on a massive Medium rant about it, Marc sent me a text. He rented an Airbnb to have family from out of town stay because his eldest son graduated and it’s consumed his world.

Dammit, I can’t stay angry at that. He had mentioned it in passing. And since I’m not in Girlfriend Mode, I can’t get pissed that I didn’t know all the details.

Marc is back in the roster.

Sean on the other hand is out. He responded to all my messages but since getting a new job that took him frequently out of town, he never initiated messages to hang out. And it dawned on me: that fucker is dating chicks in his new company’s headquarters in another state.

Which is within Sean’s rights, of course. But that dude he wants to keep me hanging around despite not making plans anymore. And so, I stopped messaging him. We haven’t spoken in over a week.

With only Marc in my game roster, I needed another player in the mix. I’m not in a position since I still live at home with my Soon-To-Be-Ex-Husband to get tied down into something serious but geezus fuck, I can’t rely on Marc for ongoing dates and sex.

Maybe I was pissed at Sean. Maybe I was pissed because the divorce mediator bumped out our final meeting for our paperwork to be filed by two weeks. Maybe I was pissed that this divorce is taking so long, I can’t move out until my name is off the home loan.

For whatever reason, I went balls-in to find another guy to date. This led me to have two dates tonight.

It is a big, big mistake to schedule two dates with new people on the same night.

My first date was with Thomas. Good looking guy, has his daughter full-time, and was sweet to me from the get-go. Given his schedule with his daughter, he couldn’t stay out late. Not ideal for me, since I’d rather go out after my kids are asleep so I don’t get flack from the Soon-To-Be-Ex-Husband.

Figuring that the date would end at 7 pm, I scheduled another date for 8:30 pm. My thinking was: I’m already out of the house with Joseph watching the kids, I’m all dolled up, why not take advantage of that and kill two birds with one stone?

My second date was with Amir, who is a hot AF Indian guy who runs an event planning business. I knew our date would be fun; how could it go wrong with someone who plans parties for a living?

Tuesday rolls around. I’m annoyed because this June Gloom bullshit is killing my outfit game. My date outfits are lacking and so are my finances to buy anything new because the goal is to put all my extra dough into a down payment for a house.

I’m cranky. We haven’t even gone out yet but Thomas is becoming clingy and desperate-like, which irritates the shit out of me. I want a guy with confidence, not someone who acts like going out on a date is akin to giving my kidney.

However, I don’t bail on things last minute. I decide that I’ll be cordial during dinner with Thomas and then get my party on with Amir. Even if things didn’t work out with the latter, it was bound to be a fun night.

I park at the same time as Thomas. He’s dressed in a business shirt and dress pants since he came straight from work. His body is much better than I thought it would be. I love when guys wear fitted shirts. Thomas is also better looking in person. So far, I’m impressed.

After we hug and we talk while walking in, I’m blown away by his voice. In my mind, his voice was a high-pitched whiny sound. It seemed natural given his neediness. In person, it was surprisingly deep. And he had incredible confidence, a complete opposite of the impression I got online.

We sit side-by-side in a booth at the bar. He admits that he’s nervous but the conversation is amazing. The chemistry is amazing. He’s amazing. The only flaw I spot is homeboy needs a manicure; that’s a pretty good flaw to find on someone since it’s easily fixable.

Our conversation goes deep from the get-go about marriage, marital sex, and a whole slew of things that I don’t even remember. He leans over to kiss my cheek. The next time he does that, I turn my face so that his lips end up on mine. Every time I say something, Thomas laughs and says that I’m unlike any other woman because of my humor and perspective.

We spend the evening giggling, kissing, drinking, and endless talking. He tells me I’m beautiful and a 10 (has anyone called me beautiful since the age of 30?). I’m cursing that I have a second date since Thomas didn’t have a hard deadline like I thought he did. I lie and tell him that since I thought he couldn’t stay out late, I promised to help a friend study for her project management certification.

I fill myself up on greasy food and only one drink because unlike my usual MO, I can’t spend all evening sobering up if I drink too much.

I’m glad I made the second date for 8:30 pm. I’m still hanging out with Thomas by 8 pm and the date with Amir is two cities away. He walks me to my car and we passionately kiss. He presses up against me and I can feel his hardness. “You’re ravenous,” he tells me in response to my moans and how my hands clutch his body.

Time for Date #2.

I message Amir that I’m running late but the GPS tells me I’m on time. My brain is racing with thoughts on Thomas and much he blew my mind. How am I supposed to go on a date with another dude after spending time with a wonderful guy?

Amir’s waiting patiently outside of the restaurant. While he’s shorter and overall smaller than I thought, he’s definitely on the mark for looks.

We grab a spot by the bar and start yapping off the bat. Amir’s talk about his event planning business is a thousand times more interesting than Thomas’ corporate job. We talk about Indian parents and culture. I make him laugh by telling him brown aunties always get their feelings hurt if you only eat four plates of food and there’s never napkins, only a box of Kleenex in the middle of the dining table.

The restaurant closes and all I want to do is get home to bed. I’m too buzzed to drive home and I didn’t want to give the impression I wasn’t having fun, so I agree to walk to another restaurant that’s open later.

As we’re walking, Amir babbles about how we didn’t need to wear masks and how he only got one shot of the vaccination because it’s 80% effective, why bother getting more? His viewpoints on Covid are a red flag for me.

We get to the second restaurant, a Mexican joint that is known for being overly pricey for not-so-great food. The music is blaring too loud, but we spend the evening talking nonstop. Not once all night was there a lull in the conversation.

The thing with very social people, such as event planning dudes, is they’ll talk with everyone. As a frequent patron of the restaurant, different staff members come over to shake his hand and yap. This annoys me; the music is loud, they’re wearing masks so I can barely understand them, and he’s not introducing me so our conversations were interrupted.

Like the first place, we stay past closing. Finally, a manager comes over to shake his hand and Amir introduces me. The conversation is long and I’m keeping my irritation on the inside; I didn’t stay out late to chat with a restaurant manager all evening.

Still, the date was fun as I knew it would be. Amir walks me to my car and we briefly make out. He’s bolder with his hands; while Thomas’ hands crept over my top, Amir’s hands eventually went under my shirt to grab the goods. After a few minutes, I step back and say I need to go home.

I didn’t have much time to reflect on the date with Thomas because of the second date with Amir. By the end of the night, my date with Thomas seemed years ago.

I message Thomas to let him know I had a fun time. He replies, “Me too! Formulating a minor crush. Need to see you soon cutie. You’re so uplifting among other things.”

Amir messages first, saying “Um you are way hotter in person”. I tell him I had fun and I loved hanging out. “Dude! Had a great time too. Thank you!” he replies.

Never again will I schedule two dates back to back. It was exhausting. It took away my enjoyment from either guy because my time and my brain were split. I couldn’t stay in the moment while having the other date in the back of my mind, which isn’t fair to either of them.

I’ll ruminate on them tomorrow. I won’t think for too long; I have a date with Marc in the evening.

I never knew dating would be exhausting.