50 First Dates: A Year Long Dating Experiment

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Sorry for the clickbait. It wasn’t exactly “50 first dates” but it was a dating experiment! Let me explain.

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Why Did I Start This Dating Experiment?

In the year 2015, I decided I would embark on an online dating challenge Previously my dating life had been terrible. My ex-boyfriend broke up with me a week after I graduated college and I fell for someone who wanted someone else (and didn’t tell me until he went to visit her in California).

It just felt like a perpetual, “He’s Just Not That Into You” and I felt I was taking this “dating thing” a little too seriously. Instead of taking a break as most people in this situation tend to do, I jumped headfirst and full force into dating.  I pledged to challenge myself to have 50 dates in one single year.

So, yes, that worked out to roughly 1 date per week, on top of working both full-time and part-time, about 60 – 70 hours a week. I was armed with my Erin Condren Planner (to help me keep track of them all), a pack of pink heart stickers, and my smartphone full of online dating apps.

The Ground Rules

Before I could start swiping away on Tinder, I had to develop some rules for this dating experiment.

Rule 1: A FIRST date must be in public. Where in public didn’t really matter to me: bookstores, restaurants, coffee shops, etc.

Rule 2: Subsequent dates may be “at home” dates.

Rule 3: I have to say yes to every date I’m asked on UNLESS I get bad vibes.

Rule 4: Dates MUST be documented by a heart sticker in my planner

Rule 5: Dates HAVE to be completed by December 31st, 2015.

To be clear, I wasn’t doing this dating challenge to find a relationship (though that would have been great!), I did it to learn more about myself and others, and to make myself a little bit uncomfortable.

The Actual Dating Experiment

January: I had a total of 5 dates with 3 different men. The most notable of which was B. B was in his late 30s, had 4 children, and was recently divorced. I went on 3 dates with B in January.

February: I had a total of 4 dates with 1 man – B. B took me to my now favorite restaurant for Valentine’s Day. He promptly broke things off when his teenaged daughter found out.

March: I had a total of 2 dates with 2 men. E was my favorite of the two, though I’ve never seen him again. We went to a coffee shop and talked for a few hours. He ghosted me for awhile and then I found a Captain America comic book on my doorstep with a note from him. I never gave him my address – so that was strange. Still have the book though.

April: In April I went on a total of 4 dates with 3 different men. The most notable of which was BR. BR still messages me every couple of months to this day to try and get me to go out with him. (Hi BR, I know you’re reading this).

May: May, like March was another slow month for this dating challenge. I went on a total of 3 dates with 2 men. I continued dating A from April. We went on a total of 4 dates and he introduced me to Howl’s Moving Castle, which is great if you haven’t seen it.

June: I had a total of 7 dates with 5 different men. One of which I still talk to periodically and one that I went on a date with all the way back in January (SW).

July: July was another low month, with 2 dates with 2 men. Nothing significant or notable about this month.

August: August was my lowest month, with only 1 date. I was starting to feel the pressure of this dating challenge. Again, nothing notable or significant about this month.

September: September was tied with August with only 1 date. If you’re keeping track, this brings our total up to 29 dates.

October: In October I ramped it up a bit with a total of 6 dates with 6 different men. One notable thing this month was I tried to go on two dates in one night -_-

November: November was my highest month with 8 total dates with 5 men. One of these men was SW. Yes, SW from June and January. We tried one last time earlier this year but it was a no go.

December: Last month. In December I went on 3 dates with 3 different men, 2 of which I’ve already mentioned (B and BR).

Total: 46 Dates!

While I didn’t hit my goal, I was pretty proud of putting myself out there. Keeping scrolling to read about what I learned.

What I Learned From this Dating Experiment

Don’t keep going back to people who only fulfill part of your wants or needs. As you read, I decided to date SW multiple times, spanning the entire year. While he fulfilled part of what I wanted and needed out of a dating partner or relationship, he didn’t fulfill everything. This is not to say that your partner has to be everything you want or need, but if you have certain standards that are must-haves, you deserve a partner who has those.

I seem to have a particular type, at least physically. I like what I like and I won’t apologize for it. Most of the men that I dated in this experiment were significantly older than me by 10 to 15 years, white, and bearded. My current boyfriend definitely fits into this (Hi <3).

I learned to have more confidence in myself. Dating can be really tough, especially when you feel like you just keep hitting roadblock after roadblock. Not taking dating too seriously allowed me to have more fun and not worry about if a relationship would come out of it.

Don’t try to juggle more than one date in one day. You’ll feel frustrated, flustered, and tired from all of the running around. If something goes wrong or if you’re just a bit late to one date, that sets up a chain reaction for the rest of the night. Believe me.

Lastly, dating is a marathon, not a sprint. Cliche right? But it really is true. Don’t expect a relationship to blossom out of one or two dates even if they were amazing. For me, it was tough to see people getting in and out of relationships so easily, when I could barely get someone to date me for a few months. My single people, I see you. Love can come when you are least expecting it and not even looking for it. Do your best to live life the way that you want to live it and find someone you want to be with because they add value to your life, not because everyone else is in a relationship.

Text that says 50 first dates: a year long dating experiment with a picture of two people holding glasses of red wine.

So would you try this dating experiment out? What would you add or change? If you liked this post, share it with a friend or let me know what you think in the comments.

Briana Hollis is a licensed social worker and self-care coach. She earned her Master of Science in Social Administration from Case Western Reserve University in 2014 and her Master of Education from Tiffin University in 2019. She has spent the last 5 years working in crisis intervention.  Her passion for serving others is the heart of this site. She started Learning To Be Free to assist others in bringing freedom to their lives.

Briana is also the author of The Self-Care Journal for Young Adults.

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  1. Eunice Abe says:

    Wow, I’ve never heard of anyone’s who’s tested this dating experiment. Well done on putting yourself out there! I’m 100% with you that love comes when you’re least expecting it because I can totally relate!


    1. Briana says:

      Thank you! I don’t think I’d ever do it again but it definitely was fun.

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