40 Dates And 40 Nights: One Woman's Quest To Find True Love On Tinder

Jamy, a 20-something serial dater, chronicles her digital dating escapades.

Tinder isn’t necessarily the place you go looking for love. An easy date? Yes. A casual hook-up? Totally. But a serious relationship with long-lasting, emotional investment? Not so much.

That is, unless you’re Jamy.

Jamy (a pseudonym to protect her IRL identity) is a 28-year-old woman from Los Angeles who claims to have "been on more dates than Carrie Bradshaw.” She’s dated dudes of all shapes and sizes, from “the third-string Colts quarterback” to a "broke writer” to an actual Backstreet Boy.


Which is why, after over a decade in the dating game, Jamy’s decided she's ready to settle down.

So how does a serial dater settle down? By going on a lot of dates. Forty Dates In Forty Nights, to be exact (with a specific set of rules). She's has been chronicling her one-date-a-night experiment on her blog with relatable, often hilarious, stories about each of her first-time Tinder meet-ups.

Jamy's just over halfway through her required 40 dates, recently switching up the scenery and heading out to New York for a visit, so I decided to get in touch with her (via email -- she’s obviously very busy) and check in on how it’s going.

Why did you decide to use Tinder as your platform versus, say, OkCupid or a service more commonly associated with promoting "serious" relationships?

I'd actually tried both OKCupid and before giving Tinder a whirl. On OKCupid, I was finding a pretty large discrepancy between the profiles and the actual people. I went on maybe five dates, and didn't find anything remotely close to what I was looking for.

Match, I had better luck but I found the process of trying to date through [the site] long and arduous. I would spend days, even weeks, emailing back and forth with guys before they would ask me out. Then I'd get to the date and we wouldn't have that chemistry.

I finally decided to sign up for Tinder, and I quickly realized two things. 1.) It was really easy to meet people and the casualness actually helped on the first date, and 2.) There were high-quality guys using it. It's lost its initial taboo.


On your first date, you said you were so nervous you had to give yourself a pep talk in the car before going in. What about this experience makes the Tinder process more nerve-wracking?

I have become SO much more comfortable with first dates. Except for my first date in New York. I had horrible anxiety going into that one, because it's a new city, and I don't live here, and I had no idea what to expect.

Related: This Guy Recreated Girls’ Tinder Photos And The Results Are Amazing

I think because you're usually going off on far less [personal information] with Tinder than Match or OKC, it can produce a lot of initial nerves. With less of a vetting process, especially with the breakneck speed I've been doing it at, you're not totally sure what you're going to get. But instead of being nervous about that, I've started to get excited.


What's the best date you¹ve been on so far in this experiment? Why was it so great?

My dates with New James. It's funny, because he was the only guy I actually told about my blog, and initially this turned him off. But after reading the first 10 entries, he changed his mind and decided to ask me out. In this weird, meta way, the whole thing makes sense. I joked when I first began this experiment that I was turning my life into a rom-com, and my date with James really solidifies that statement.

Related: Now That Britney Spears Is Single, Check Out Her Tinder Account

Which date was the worst?

Oh god, Date #9 for sure. Spoiler alert, but who invites someone on a first Tinder date on their 30th birthday? It put me in a really awkward position from the second he told me after I sat down, and then I felt responsible for showing him a great time, even though I really wasn't connecting with him.


What about the weirdest?

Date #19, That Awkward Anniversary. It's all in the title. We were not connecting at all, and the conversation was so strained, and then the waitress brought us an anniversary dessert. It actually felt like a movie. My date even said he felt like we were being filmed. (Nope, just blogged about.)

Have you learned anything surprising about dating during this experiment? Anything insightful you didn't know or weren't expecting to learn?

It's really important to go into each situation without any expectations. If you start to assume things about a person before you even meet them, you risk not really showing up for who they actually are. You might be initially disappointed by their appearance (Date #3) and then let that influence you the rest of the time. Date #3 actually ended up being a decent guy, but it took me a while to see that because he hadn't been what I expected.


Conversely, if you go into it anticipating the worst, that's probably what you're going to find, even if they might be a really cool person. We all have flaws, and if you go into every date hunting those out, you're never going to find love. The best thing to do is go in neutral and open. At the very least, you can connect on a human level. And isn't that what this whole dating thing is really all about anyway?

You're just a little more than halfway through your experiment. What are you hoping to get from the second half?

Sleep! I'm kidding. But not really. This has turned me into a bit of an insomniac, and it's incredibly time-consuming. But one of the most rewarding experiences I've probably ever had.

Related: 15 Food-Related Tinder Lines That Will Make You Vom In Your Mouth

But after coming to New York (for my third date with The Cab Driver) and experiencing the city again, I'm starting to think that some deeper things are at play. I'm trying to be very present to what the world is showing me right now, in terms of where I'm living, my career, my love life. It's all incredibly exciting. And sleep-depriving!


If anything more comes from this blog beyond my own personal growth and the connections I've already built, it will just be icing on the cake. But I will say that I now have a pretty solid idea of what I want to do for the rest of my life. And it's so simple, something I already knew, but has become reinforced a thousand-fold: write and love.

Follow Jamy's quest to find true love on Tinder on her blog 40 Dates & 4O Nights.