Written by| Jamie Cabral

Along with being branded as a “hipster in denial,” my friends and colleagues have reassured me on numerous occasions that I am in fact a “serial dater” as well. At first I was somewhat horrified by the fact that the people I am surrounded by on a daily basis think of me as someone who frequently spends her evenings out on dates with random gentlemen. After three years of serial dating, I have come to embrace the fact that I am in fact, a serial dater. I am not exactly sure who said it, but I once heard that you have to kiss a lot of frogs to find your prince. Metaphorically speaking that is. Most of the men I meet don’t make it to the second or third date; therefore there isn’t much kissing—if any taking place.

Dating in this era has pretty much become a second job and you can thank the 1920’s prohibition era for all of the extra work you have to put in to find love. During the 1920’s, women were becoming more comfortable with their sexuality. Casual group dating was becoming more common, divorces were becoming more frequent, and marriage was on the decline. Thanks to the development of birth control, women were becoming more casual with sex too. Evenings were spent at speakeasy’s drinking gin, smoking cigarettes, wearing more revealing dresses, and listening to jazz. Men didn’t need to recite romantic lines from EE Cummings, open the car door, and wait for marriage to sleep with a lady. After a few hours of jazz and four drinks deep, the clothes came off, courting went out the window, and you and I now have to put in strenuous work to find love.

With dating websites like Match.com, Eharmony.com, and POF.com, you would think dating would become a tad easier. Although the quantity of single men and women online has increased, the quality of people online has greatly decreased. (The same can be said for the quality of people out in the real world as well) Falsified profiles plagued with terrible grammar, shirtless bathroom “selfies,” and self-descriptions such as “I like laughing and eating,” (Uhhh who doesn’t enjoy laughing or eating?? ) are enough to make you roll your eyes and laugh hysterically at the stupidity of it all or make you throw up a little in your mouth. Whereas online dating was created with the intent of helping people find relationships, it’s quickly becoming a place to scope out your next bed buddy until something hotter comes along.

The first time I joined websites like Match.com or POF.com, I found myself sifting through over a hundred emails within a few days. I was taken aback for a moment in the beginning, that this many men found me attractive and were interested in pursuing me. After a long work day, I would come home and spend some time each evening answering and deleting emails, and flipping through profiles of various ages of eligible bachelors. It was like an online shop where I could flip through and find the best selection for myself. Every day that I looked, I found someone better than I did the previous day.  It felt so unnatural. What happened to people meeting at the grocery store, through mutual friends, or church? And how could I ever be satisfied with one person when if I kept browsing through different profiles, there would always be someone more intriguing than the last?

Within a three year period, after various dates with men I met online, and a few that had the courage to ask me out while out in the normal-non-cyber world, I would find myself having a love-hate relationship with dating.  On one hand it was thrilling to be meeting someone I had never met in person. There were so many possibilities! But on the other hand, it felt like exhausting labor. I had to dress up, show up, and hope they didn’t look like Cousin It or end up being the next Jeffrey Dahmer. And how did I know we were on the same page by the end of our date? I was beginning to feel like dating was a game, where both players had no idea of what the rules were.

During these three years, I met several men who would surprise me and end up being more attractive in person, some who had very little resemblance to their photos, or were much shorter and heavier than described. I spent one evening out to dinner with a man who boasted for hours about his prominent family members who had all studied either law or medicine and how as a child he collected his finger nail clippings for years. One man got increasing louder and more obnoxious with every drink that went down, drawing attention to our table. Another asked for sex on the first date. The nerve. Often times, I found it hard to decipher whether or not someone was being genuine about pursuing a relationship or putting on a good show to try and get me into bed with them. It always seemed like a guessing game.

Not all my experiences have been negative ones though. I once met a lovely gentleman who drove two hours just to take me out to dinner and would spontaneously kiss me in the rain just like a scene from an old film. I’ve had a fourth date floating out on a lake in a boat with nothing but a black starry night sky surrounding us while listening to old classics by Frank Sinatra and Otis Redding.  I’ve met intriguing artists, businessmen, and world travelers. I’ve gone out on dates with men in various cities that I’ve traveled to. One afternoon while in Manhattan, I met up with a former designer for Michael Kors and spent the day jumping in and out of the subway while he gave me a grand tour of the city. We chatted about vintage and life over tea at The Roebling Tea Room late into the night and walked through Central Park.  I’ve met men who made me excited about dating and that I hoped I would see again. Some helped me to put aside my somewhat cynical views and remember that there are good people still out there. Some have become my friends, learning lessons, or now ex-boyfriends, but I have certainly gained some knowledge and learned many lessons from each person I have encountered along the way.

I’ve learned communication is truly key in all stages of dating, as well as life. One must make their intentions and what they are willing to tolerate and not tolerate, very clear. A few gentlemen have taught me that it’s not always best to put all of your eggs into one basket. In other words, keep your options open. If someone hasn’t made any sort of commitment to you and you haven’t established any exclusivity, than go out to dinner with your attractive neighbor. If you aren’t interested in dating other people, refer back to line one… communicate what it is that you want from that person. Always follow your gut instinct, not your heart. Your heart can lead you into some troubling situations and often times can cause us to forget to put logic into the equation. (Like the time I packed all of my stuff and moved to a city for a guy) This is a challenge for most of us, especially for me and my sentimental heart. But trust me, your gut knows what it’s talking about! Something I’ve learned many times when dating someone for a few months—the beginning is as good as it’ll get. If dating a person in the beginning is plagued with more unpleasant times, than good ones… move along. The first several months of dating should be the most exciting months you’ll spend together getting to know each other. Don’t settle for anything less than exactly what you deserve!

The most important lesson I have learned from being a serial dater— The Universe allows things to happen when they are supposed to happen. Yes, I truly believe everything happens for a reason. A few of us may get lucky in the online dating world, find love, and meet our future spouse, but let’s face it—this isn’t the way people were meant to meet and perhaps it’s time I retire my serial dating ways. After all, the best relationships happen unexpectedly, under the most unlikely of circumstances, when we stop trying so hard to find it.



  1. I would proof read a bit more, there are a ton of grammar mistakes.

    What is serial dating anyways? Dating is implied to be taking place more then once. If you’re not dating, or single you’re in a relationship. It’s like saying you’re a serial driver, or serial breather, or a serial eater. Now a serial monogamist, or someone who goes from one relationship to another could be something, but a serial dater, it just doesn’t make any sense.

    You should just call this ‘my experience with dating’ because its not unique or inspiring it’s just , just 1 girls dating experiences.

    Seems to be a vapid editorial really; “I met a guy, they were cool, i met some other guys, they were not… you should be honest.. dating is hard…” all things that are as common sense as ‘close cover before striking’.

  2. The last sentence was a solid way to end this piece. A very honest glimpse into the mind of a serial dater. I loved it. When you look for love, you almost force it. Which never ends well. Other times we meet someone when the timing isn’t right in their lives (or ours). True, honest, REAL love will always find its way. You sound like a true catch, any man is beyond lucky to have had the opportunity to accompany you on a date. You need to write more on here.

  3. It does seem to be a difficult time for dating and the likes. I know a lot of people using online websites. several have gone on to be in really long term relationships. there is always hope out there. keep having fun with it! 🙂

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