Five things I’ve learned as a serial dater

Note: This is part of the series “31 Dates Before 31” in which I will attempt to go on 31 adventure dates before my 31st birthday and raise money for the Domestic Abuse Council of Volusia County. 


In the last five weeks I’ve been on 20 dates, which is more than I’ve gone on in an entire year. While I still have 11 more dates to go on, I’ve learned a lot about myself and dating in the process.

Our phones have become game changers in the world of online dating. Never before have we had so many options at our fingertips. And while there are dozens of potential suitors in the palm of my hand (literally), why does it feel so hard to find a compatible partner?

This challenge has given me more insight into how I’ve approached dating in the past and why it hasn’t worked. By setting up fun and adventurous dates, I’ve taken the focus off of finding “the one” and instead just had a good time. When you take away expectations, dating actually become enjoyable instead of demoralizing.

I’ve used Tinder for 80 percent of my dates, and I’ve found it to be the best tool for setting up dates on the fly, but it can also feel like a game of musical chairs in which everyone has shiny object syndrome.

While it’s still too soon to draw any hard conclusions or say for certain if there’s any real romantic possibilities with any of the guys I’ve gone out with, here are five things I’ve learned so far:

  1. People flake, a lot

If I had to guess, I’d say that every 1 out of 3 dates I’ve planned has fallen through or been canceled. What’s frustrating is that it means I am spending a lot of time texting and conversing with guys, coordinating schedules and planning fun dates only for them to be canceled last minute.

Take for example a guy from Jacksonville who I will call Jim. Jim and I hit it off on Tinder and after we bought tickets for a paranormal ghost tour at the St. Augustine Lighthouse I realized that we had booked them on the night of the city’s 450th year anniversary celebration, which presented a logistical nightmare because of traffic and road closures. Being the type A person I am, I broke out maps, consulted with a friend who lives there and picked the brain of a travel blogger to determine the best possible way to navigate the area and avoid crazy crowds.

Just a few hours before we were set to meet, I texted Jim to make sure he knew where to go. Apparently he had come down with a stomach bug and couldn’t make it.  He assured me he still wanted to meet and felt horrible to break off the date but he just wasn’t feeling well. I moved our tickets to the following Friday and we rescheduled. The day before our rescheduled date I reached out to Jim to set a meeting time. He canceled our date again, this time for “personal” reasons. When I pressed him for a better excuse, it turned out that he had met someone else who he really hit it off with a few days earlier.  I may have not reacted as gracefully as I should have because at that point I was BEYOND FRUSTRATED with the amount of time I had wasted.  Unfortunately this has become somewhat of the norm in the dating app world, at least in my experience.  At least Jim responded though. Most just go silent.


  1. Tinder is not just for hookups

The first question I get when I tell people that I’m using Tinder for the majority of dates is: Isn’t Tinder just for hook ups? Swiping yes or no to match with a guy based on a few photos and one or two sentence descriptions, does make things more surface level but It’s easy to weed out the guys who are looking for hook ups because they make it pretty obvious. I’m always clear about my intentions and I think more people are using Tinder to find meaningful connections.

I for one do not have time to write a cover letter to every person I want to go out with and “pitch” myself to guys on online dating websites. Because I live in a tourist destination, I’ve found that a lot of guys who are in town are looking to meet up with locals to explore the area and because the dating pool  is so small in Daytona Beach, Tinder helps me meet up with guys I otherwise wouldn’t come across.

  1. Profiles don’t fully represent someone

I’ve gone out with guys on this project that I may have turned down based on their profiles but after meeting them in person they are a lot more attractive or interesting than their profile suggests.  Online dating is so one dimensional and based on looks that it’s frustrating. And we often forget that sometimes voice, mannerisms, intellect and personality are what makes a person attractive.

And this works both ways. I still feel the sting of a guy who canceled a date with me last year because he couldn’t tell if “I was fat or not in my profile photos.”  (To be fair he didn’t offer up this excuse off the bat, I had to press him on why he was canceling.) I felt like that was such a rip off because while I may not be a size 4, I think I’m pretty fun and interesting.

Through this project, I’ve learned not to make snap judgements. Because it’s the guy who looked a little nerdy in his profile photo who was actually sweet and fun. The guy who appeared to be a snob and fake was actually down to earth and genuine. And the guy I thought I’d have no attraction to, was the one with a great smile and personality.

  1. If you aren’t having fun, what’s the point?

Prior to starting this project dating went something like this: I googled the hell out of my potential date, stressed about how the date would go for days/hours leading up to it, got so nervous on the date I had a habit of using alcohol to calm my nerves (never a good idea). If the date went well, I stopped pursuing other options and crafted strategic responses that played out in a texting conversation more akin to a chess match. If the date went bad, I felt hopeless and took it as yet another sign from the universe that there just wasn’t someone out there for me. Dating had the potential to create so much anxiety for me that it didn’t seem worth making the effort.

But this project was meant in a way to get over my dating hang ups and just have fun. As a solo traveler I have no problem doing things alone but I’m realizing how much more enjoyable new experiences can be in shared company. By planning fun activities on dates, I’ve realized that most people want to have fun too. I think we often want to feel someone out before jumping in a kayak with them or engaging in any activity that requires us to get sweaty or dirty or go out of our comfort zone on a first date.

But when you are staring at a person across a table or bar, dating can feel like a job interview. I’m at my best when I am experiencing something new and being in my element has taken the anxiety out of dating. It’s also been a test of sorts: can you hang on my level?

  1. It’s not me, it’s you

When we have a constant portal into the highlight reels of others’ lives, the first thing you tend to ask yourself is: Why don’t I have that too? I’ve felt this more as my Facebook newsfeed seems to get filled with more engagement announcements, wedding photos and baby pictures by the day.

But instead of seeing myself as the problem, I’ve realized that where I’m at is a result of taking a different path. I have worked really hard over the past decade to establish myself in a career that I love, buy my own home and make traveling a priority.  I’m happy where I’m at but it’s a bit more difficult at this age to find someone who is in the same place.

As my friend Barb put it, all the guys who are established and have everything together in their 30s are usually already married. Couple that fact with the demographics of Central Florida (Looking for a single man over 60? We’ve got plenty!) and it really it isn’t a surprise that I’m still single.  So instead of seeing my singleness as a “problem,” I’m starting to see it as an opportunity.  I have the freedom to create the life I want and hopefully at some point that will lead me to someone who is on a similar path.

To find out more about my dates, sign up for the newsletter at the right. In effort to promote healthy relationships and help victims of domestic violence, I’m asking for donations to the Domestic Abuse Council of Volusia County in lieu of birthday gifts this year, which you can make by following the link below.



Leave a Reply

Your email address will not be published. Required fields are marked *