
Unfortunately, most first dates do not go the way of the classic Blink-182 Anthem, instead, they usually end with one participant needing to go home to clean their cat’s litterbox at 8:30. Increasingly so in the age of dating apps.
I can say this with a certain level of expertise, having recently concluded a run of about 8 first dates over the span of 3 weeks. This was unintentional. I have tried to avoid packing my schedule with dates thus far in my journey because it leads to emotional exhaustion. It’s better to only go if you’re excited. Gives it a better chance. Five of them were through dating apps, two were girls I met in person, and one was through the AI dating service.
For me, I enjoy dates because I love meeting new people, getting to know them, and talking too much. The problem is that girls have extremely different expectations about what a first date means. In fact, the biggest problem with these first dates is you have no idea what you are getting into.
Some girls expect reservations at the ice skating rink, followed by a 4-course dinner with a carriage ride as the cherry on top for a first date. And they say so in their profile. Others explicitly lower the stakes, asking to keep it casual and take it slow.
I’m unsure what the best approach is. Keeping it casual nowadays leads to texting 6 different people at the same time and ending up in a series “situationships.” However, the alternative can be positively alarming. People can get very attached on a first date, which makes the whole process very uncomfortable. Leading to my next point…
When going on a blind date, the other person is unknown. Maybe they wear an unexpected monocle🧐(It’s making a comeback!), spontaneously break out in rap battles at the slightest provocation, or grossly misrepresent themselves in their profile. There are many reasons why it may not work out even if the date is enjoyable. Putting pressure on someone you haven’t met yet is a losing proposition.
But, if you aren’t excited, then it really is pointless. Part of falling for someone is the excitement of discovering them. But, you don’t want to be too picky. Someone might surprise you. But, should you go on a second date if someone has good qualities, but you didn’t feel any chemistry? But.. But.. But
My goal is full presence in all my interactions. Practically, that means limiting online dating to girls I am truly excited about and focusing on meeting people in person.
When meeting people in-person, you can see their good qualities gradually in a pressure-free environment. But after a first date, you have to decide if you want a second and how much time you want to invest. I may be accused of fishing for information or intimidating the witness, but my top question on a date is: “What do you love talking about most?” Helps me cut into the core of how a person thinks about themselves. Though, unfortunately, I am sure there are great people who would struggle with that.
There are no perfect solutions. I’ll trust my intuition. Cheers!












