Dating Multiples – Tinder Tumble: Six Date Stumble – Part 2

Theodore Roosevelt once said, “Comparison is the thief of joy.”

Ask any dating expert, as in real “experts” other than me, because you should not be here for advice, they will say the key to successfully dating online and potentially meeting your match is to compare and contrast multiple people in real time by pitting them against each other to gage what you like and what you don’t, versus what qualities are important against those that aren’t. This is fact, however, just because I’ve stated it does not mean I’m either for or against this concept, not am I convinced that this type of dating works. I’m simply stating the facts, because I’m single and well aware that maybe this was a reason as to why it was so. I’m also the type of person who is ok with recognizing my own deficiencies and not shy about seeking advice from people who know more than me.

In this case, why not bring in some advice from the experts, because whatever I was currently doing was not working.

I didn’t know anything. I haven’t gone on any dates yet. I haven’t met one person. Hell, I haven’t even downloaded the app yet! But what I did know was – if I was going to be dating multiple people at the same time to increase my chances of meeting someone great, it’s also safe to say that in order to accomplish such a feat, I would have to be dating everyone “somewhat” casually with “some” detachment, because the minute I became too serious too early by spending all my time with one guy, all the others would fall by the waste-side and the whole comparing/contrasting system breaks down.

I also knew that the people that I was dating were also highly likely to be also dating others. That is online dating and if I didn’t as well, I felt that would put me at an immediate disadvantage. I would end up chasing the guy, because all my attention was on him while he was still exploring his options. He would have all the power and I would end up with all the hope! Furthermore, why would I want to tie myself up with one guy while he’s maximizing his chances by seeing other people? Why would I want to fixate on him when he’s intentionally or unintentionally comparing me to others, while I’m running around talking about the great guy I met? I had to play too if I didn’t want to be caught in a game where he was the star pitcher and I was the rookie. This was going to be an equal playing field where both parties would be dating multiple people. I had to!

And if it turns out that he wasn’t dating others after all? Then this would be a first time where I would finally have the upper hand. I would still win! At least that is how I translated these pearls of wisdom as it pertained to me and how I date.

I was not someone who ever dated multiple people at the same time, mostly due to the same challenges that many people who have given real dating a worthy effort would say. The truth is, it’s difficult to meet one quality person to go out with, let alone multiples within a specific period of time. For better or for worse, this style of dating and my history with men turned me into an unintentional, monogamous dater. I’d meet someone great, we hang out for an x amount of time and either go our separate ways or not. Since I was only meeting and dating one person, my feelings naturally intensified because all my attention is on one person at one time. If I really liked him, he would win. But what would happen if I was lucky enough to snag more than one great guy at the same time?

Would these same guys that I attached myself to in the past still win if there were others? Could I compare them like the experts said to do? Would this type of dating help me see the type of man I was meant to be with?

Honestly, the whole concept of dating this way seemed out character for me from the very beginning, but that didn’t stop me from trying. I was determined to keep my options open and learn how to play the field. I was going to date! I was going to be the confident, cool girl who had options! I was going to be the star pitcher!

The only problem? Not only was I right about not being the type of person who dates this way, but I didn’t do any of the things in any of the ways that I meant to do them in.

In other words, I should have just admitted that I was in fact a serial monogamous with a big heart who decided one day that I was going to be a pick-up artist on the straight person’s, Grinder.

*There are roughly 54.2M single people in the US with an astonishing 41.2M admitting that they have tried online dating. Of that number, 53% have admitted to dating multiple people at one time, but only 20% of current committed relationships result from a dating site.*

I’m not a mathlete, but even I see that there’s something strangely amiss here.

How can we be dating more people than ever, yet have more single people in the US than ever? How can we be dating all these people at the same time, yet so many of us are still not in committed relationships? How is this type of dating altering the way we find love? (Linking to a brilliant article called, 50,000 First Dates: Online Dating Makes Finding a Partner in NYC Harder Than Ever).

I would find out within minutes of downloading Tinder, because even though this was supposed to be a dating (hook-up) site, I instead felt like I was entering an alternate reality that was crossed between an electronic orgy and a strange, secret addiction. And when I say addiction, I’m not exaggerating.

The first few days, I was a Tinder Fiend and it’s not because the app was so fun. It actually crashed my phone so many times that I was beginning to thing that my horoscope had changed her mind and was trying to tell me, “Jennifer, this isn’t good for you. Please get off now.”

So I did what I usually do when I receive signs for the heavens, I ignored them and instead fueled my addiction, which turned out to be very similar to gambling by playing at work and staying home at night (because I was way to embarrassed to check my matches in public). And just like gamblers who are addicted to the idea that the next game might be the next win, I was addicted to the idea that the next person could be the one that I was supposed to meet. I was confused and overwhelmed by the idea that any one of these potential matches could maybe be great for me. How was I going to focus these mindless swipes into something real? Were all these options really for the best? Would they help me narrow the field or leave me wanting more?

Catching Up: Tinder Tumble: Six Date Stumble – Part I

Published by


J is a happily single 30-something currently documenting her stories of love and loss. Her blog, “I Quit Dating” features excerpts of her journey as she reflects on the lessons learned from the men she loved. A complete collection of essays detailing her walk away from finding Mr. Right in order to pursue a more fulfilled life will be self-published next year. She recently moved from Los Angeles to New York. Contact: iquitdating (@)

9 thoughts on “Dating Multiples – Tinder Tumble: Six Date Stumble – Part 2”

      1. Well, it makes perfect sense to tailor your profile to make it more alluring, but of course it seems so very unromantic. That said, online dating is unromantic by design. It’s like people shopping. That doesn’t mean you can’t have a romantic experience with someone you met online, heavens no. But the act of online dating is inherently dehumanizing to me. So, at the end of the day, hell yeah work your profile. It’s simply a means to an end. You just want to get someone else’s butt into a seat across from you so that the real deciphering can begin.


  1. Wow, you so sound like me. Which is a good and a bad thing, part of me thinks if someone as amazing as you also struggled to meet someone then I’m not such a freak, but also it means I am now secretly hoping I too will meet someone amazing after a short period of time!! (not that I know how your story ends, but I hope it is happy!)


  2. I have a serious love/hate relationship with Tinder. I love it because there are so many guys, literally at my fingertips. I hate it because it just fuels this idea that we have to play a game to date and (hopefully) “find the one.” I just wish dating were as easy as it is in my head. Ie – every guy I really like just happens to like me too and not play games.


    1. Exactly! Or if they don’t like me, just stop the charade!! I think that is my biggest thing. Thanks so much for coming by and commenting! Hope you will again!


Please Share Your Thoughts

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s