Context: I'm traveling in a big city for a month. I pulled all these dates from Hinge. Not sure if it's a summer thing or whether the city is always like that, but girls are very eager to meet up. It was much easier to schedule the dates than in my home city.

Logistics: I set up the dates at 11am, 2pm, 4pm, 6pm, and 7.30pm. This tight schedule left little room for error. Other than the last date which was a second date, they were all first dates. I tried to keep them geographically close, but they did involve two cross city trips and at least 10 minutes driving between them plus finding parking. This meant I had only about an hour and a half for each date (except the first one). I also met up a colleague for breakfast before the first date, so I had 6 meetings overall and eventually spent 12 hours outside on a hot day.

Strategy: My strategy was to be as straightforward as possible. Since every date was 2 hours max with not much opportunity to change location, I was determined to build attraction fast with humor and body language. I relied on many canned jokes and stories that have proven to work. I made sure to always sit next to each other instead of across, in order to break the touch barrier as early as possible.  

11am, Date 1 (finance girl): The location was a coffee shop. The girl had texted me at 10 that she wanted to meet half an hour later. Since this was the only date with a three hour window, I just texted back "sure". For the other dates, I was determined to say "I can meet later but I have to leave at xxx" in case of delays. If I had had only two hours, it might have messed up my whole schedule and confidence, but it turned out great.

When she finally showed up, she was a little less attractive than the photos suggested, and she was wearing awfully cheesy clothes (yoga pants and flashy high heel sandals). Either way, I'm determined to be charming. We drank coffee at high tables and she's immediately responsive to my light touching. In fact, she comes closer and closer, and after about 20 minutes she leans her head on my shoulder. Another 15 minutes or so we start kissing. I suggest going for a walk. I grab her arm and we are headed out. I suggest that we drive to a nice place after walking a bit, but she's not cool with that. Instead we walk to a park, with more kissing and heavy petting there. At some point she's putting my hand on her butt and the vibe is clearly very sexual. The pandemic has been long, hasn't it...

After some time, I'm worried it's time for the next date and I say I've to leave soon. She reluctantly accepts my offer to drive her home and once in the car, it escalates. She even pushes for sex, but I'm not particular excited about being arrested for public indecency in a residential neighborhood, so we settle for a handjob. This was a messy endeavor,  and after that I rush to drive her home.

2pm, Date 2 (physician girl): I'm running a bit late for date two but luckily so is she. I'm feeling a bit insecure because I clearly smell of vagina/cum and my shirt is a little wet. But I also feel less pressured. We meet at a hip coffee shop that mostly has table seating but also some stadium seating, so I explicitly say: "let's sit on these, i don't want to sit across." She's wearing a very cute short dress, and despite the fact that I had an orgasm just 30 minutes ago, I feel eager to connect.

The conservation is fine and she's not resisting my touching and holding her hand, but at some point I get more and more disqualifying answers. The chat turns boring after she realizes that I'm new to the city and gives me a lot of advice/recommendations. This is clearly a sign of lack of attraction, and she does not see me as a leader. I get extremely bored and head for the restroom. I check the time and I have plenty until the next date, but I decide to cut my losses. We shortly move to the patio with some more stale conversation, then I suggest to go and I hug her goodbye. Definitely a failed date.

4pm, Date 3 (consultant girl): Date is scheduled at a coffee shop/gallery crossover, but when I arrive early, it's closed. I quickly check some alternatives and luckily there are some restaurants around. This city is awesome for dating actually, because most restaurants also have a bar setup. The girl arrives and she's a lot less attractive than her photos (which were already not very attractive). She's very shy but follows my suggestion to check out a different place. We end up at the bar of a fancy Portuguese restaurant. Note, it's about 4.15pm now and I haven't had lunch. Unfortunately, this is a $$$$ place. We order coffee and I get an appetizer as well to bridge hunger until dinner.

The girl is really badly shy and barely speaks. There's also zero eye contact. Since I'm not very attracted, I'm not very cheerful to her, but I do practice my routine jokes and touching to make it more natural to me. The bar keeper at the very small bar must die a thousand deaths by listening to our boring conversation. At least the food is excellent. I again escape to the bathroom (I drank a lot of water on this hot day), check the time, and decide to cut losses. I suggest to leave and walk her to the car, hugging her tight, and tell her to text me when she gets home. She later texts me that she "had a great time". Okay, girl. If you had a great time, then maybe try to give me a good time too instead of just silently sitting in your corner...

6pm, Date 4 (attorney girl): Despite my tight schedule, I'm actually 25 minutes early to that one. I quickly consider buying a toothbrush and toothpaste to freshen myself up, but there's no Walgreens on the way. I text the girl that I'm early and that she should come out now if she can. She agrees but in the end she just arrives 5 minutes earlier. Again the place I picked is closed, but there's another bar I know just across the street. This is a good city. There's a moment of awkwardness with the bar keeper when I order the same weird drink with him that I did last week with a different girl, but fuck it.

The girl is a lot bonier than I expected, but still cute and quite charming. She's a bit shy, but smart and funny in her own way. I typically don't do well with her demographics, and I feel slightly insecure about appearing not confident. We talk a lot about psychology, and at some point I mention how boys become nice guys. She mentions that she hates those kind of guys. I keep touching her hand, but I'm ultimately unsure whether she is attracted or not.

Another bathroom run confirms that I have to head out for the final date. I walk her halfway home, and when it comes to say goodbye, she's actually very eager to kiss. While kissing, she asks me what I liked about her profile. I laugh it off and say that she has an "overall decent profile". I gently slap her butt and send her off, then run back to my car.

7.30pm, Date 5: I spare you the details of that date. It's a second date eating pizza. It's now 7.30pm and I'm freaking starving. Despite running low on energy, i try to be cheerful and make good conversation. The girl is very into me and I can let my guard down a little, just enjoy the food and later a walk in the park with some car make-out.

Afterthoughts: It was a long day and I'm freaking exhausted, but at the same time I feel great and very confident. Out of the 5 dates, 3 went very well. I got rejected once and one more was just plain boring. I was lucky that the first date led to a lot of excitement and lowered the pressure on the following ones. I was also lucky that it panned out logistically. My tight schedule could have easily blown apart if a different girl had been late out if i had not checked the time.

Learnings: The date marathon mostly reaffirmed what I already knew, but made it even more obvious to me: When on a date, go all-in. The time is NOW to be confident, cheerful, to engage in positive body language, and to have a good time. The tight schedule also made me feel that the next girl is just around the corner if this particular date fails, making me outcome independent and confidence. Girls love confidence. Build that confidence and then project it.

Also, for God's sake, never sit across on a date. Always sit next to each other and break the touch barrier as soon as possible. For me, it was very important to have a routine of stories and jokes. They work and even if they become boring to you, they serve as the foundation for more interesting conversation. To keep them interesting, I try to deliver them better and better every time.

Conclusion: It was a great but also exhausting and costly adventure. I definitely had a caffeine overdose that day, but I still draw confidence from the experience. I will probably do a similar thing in a few months and see how I progressed.