I Went On 29 Dates In 30 Days, This Is What I’ve Learned.

A detailed journey into a month of sex and double-booking.


Dating in your twenties, we all know, is a wild ride. Either you love it or you hate it… Who am I kidding, we all hate it. It’s typically a mixed bag of wrong guys, drunken hookups, maybe finding the one and trading it for the fuckboy that is sexually woke.

Dating 29 men in a month was certainly an unprecedented idea and came to me in a moment of perdition and despair. I was coming back home from yet another Bumble-date, followed by another shag followed by my beloved walk of shame. Something was off, all my dates were ending and beginning in the same way: sex.

Don’t get me wrong, I’ve never been one to shy away from a good night of steamy sex but at this point I was getting hungry for answers. What was I doing wrong? I wanted to understand more in detail, what was not making people fall in love with me or at least call me the next day. (Eliminating the nonexistent possibility of being bad in bed, of course.)

To embark on this journey I needed a system.

Dating Apps Become Your Best Friends

30 days of dating sounds a lot and it is. Tinder, Bumble, Raya were always in reach. At first I was extremely picky, as per usual, then I realized how my own obtuse research was precluding me from a fairly large pool of people, whom under normal circumstances I would never have met, but in the case of this experiment I saw no reason not to meet.

Dating apps don't have the same kind of guys. I soon realized that on Tinder there was a vast, vast choice, but not totally skimmed. On Bumble, on the other hand, I was meeting extremely interesting people, not just looking for a fuck. Raya is a fortress hidden between too many walls and hiding a group of beautiful and rich men, who are more interesting than the others? No.
If you want my advice, stick to Bumble.

Double-Booking Saves The Day (If You Hold Back On The Alcohol)

Going out every night and not having an evening to myself seemed excessive, so I realized from the beginning that going on two dates on the same day would be my lifesaver, and I was right. Squeezing the extra date for a lunch, with the occasional name mix-up, worked wonders.

One thing I had not accounted for when I started this was the money spent, the alcohol drunk and the food ingested. The alcohol was definitely a problem when I had to divide myself between two people on the same day. My memory would get foggy and I would start to confuse the stories of the two. I also don't recommend sleeping with two men on the same day, feasible but problematic in the long run.

And here I come to the very first lesson out of the three I’ve learned through the experiment.

After Awhile It All Tastes The Same in The Dark

By the 15th date, when the curiosity of getting to know new people was fading, after several beds undone and made in the morning, still in the dark about what wasn't working on my dates, I realized that sex tastes the same with everyone eventually.

There's the guy with spicier tastes (thank God), the one who likes a quickie, the one who wants to kiss you and hold you like you've been engaged for years, the one who plays you his favorite music afterwards, the one who tells you about his life like you're two old friends, but either way, sex on the 15th date tastes like an hour I could’ve spent reading more.

There are a plethora of different men out there, but the reality is that many of them, if they don't have the girl hidden or complicit, are taken, emotionally occupied, which makes the acquaintanceships always difficult. Which takes me to the second point.

Men, They Are All Hung Up On Something Already

Sebastiano, the I-just-got-out-of-a-7-years-relationship guy. We didn’t fuck. We kissed, it was sweet, I never heard from him again.
Alberto, the-monologue-guy. He talked about his childhood traumas for 2 hours. Usually on first dates I offer to pay, in this case I
considered his paying a fee for the session. I have avoided him since that day.

Michele, the I-wish-she-was-still-here-but-we-should-still-fuck. Again, treated like a therapist, I left after the first glass of wine.

All these men, attached to the ex-girlfriend who left them years ago, or attached to the idea of that one girl who was perfect but in the end, got away. All of them. Except for Giovanni, and this gets me to the last, most important revelation out of the experiment.

Revealing Too Much About Your Past Will Alienate From Some People

Giovanni, the cute actor.

Aesthetically beautiful. On the first date he brought me a book of poetry, the modern bouquet of flowers. I slept with him right after.
With him I tried something different, I didn't tell him everything about my past, I left some parts out, and as much as I don’t like to say it out loud, not unveiling my black and polluted past, rich in men and stained by a depressive period, changed the outcome of the date.

No trace of depression, no trace of murky past relationships completely altered the way I was perceived. Suddenly I was more appealing, sex could easily be taken out of the table and a second date was an option. Giovanni was an option.

Consequently, an interesting thought started forming inside my brain: Is censoring a part of oneself, at least on a first date, the secret to starting a potential relationship? I can’t say for certain, but after a few dates with Giovanni, I couldn’t hide my history and I stopped seeing him.

One thing is certain: I had not begun the experiment to seek love, but rather to understand what drove men away and I might actually have stumbled upon one last, important truth: some things are better kept in the dark in order to find the perfect match.


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