Some Things I’ve Learned from Online Dating


I’ve done a fair amount of online dating over the years, mostly on and OK Cupid. And the more I dated, the more I learned – not about others, but about myself.

First thing I learned was totally Buddhist and stuff, seriously. I really got in touch with the concepts of letting go and non-attachment. When you are online dating, you can’t start decorating the Christmas tree with a potential after a) reading their profile, or b) emailing them. The art of sending out a note into the ether and then letting go to any attachment of it returning to you is paramount to online survival. It is amazing what happens out there. Unlike in face-to-face forums, say like a bar, or a coffee shop, or on the street, people online have really honed their avoidance skills because they aren’t directly in front of someone. I’ll be the first to admit that I have completely ignored an email reaching out to me because I didn’t find the person’s profile compelling, I didn’t find them attractive, life got in the way, or I just had online dating fatigue. I know, I know! I sound like an ass, but this is how online dating works. And in some ways it is a relief because you can throw out an email, if it sticks – great. If not – well, that’s okay too. This online dating experience has actually helped me to let go more in life and be less anxious because for the same reasons I didn’t get back to someone, they may not get back to me. I don’t know the reason why they aren’t getting back to me, so I don’t take it personally (more on that in a bit).

Another great life lesson is to trust your instincts. One of my bosses calls this a tummy check. If your tummy says something’s up, it probably is. For example, when I first got online, I thought it would be good to go out of my “comfort zone.” People, testing your boundaries can be and should be an amazing thing and you should do it often, but I’m here to tell you (well, at least for me), it isn’t the best idea online. Don’t keep trying to fit that square peg in a round hole, like I have. If you don’t find the person to be a fit (for whatever reason) from their profile, chances are they aren’t going to be a fit in real life. “Wha?” I can just hear you saying, but after more dates than I can’t count, I can say that if their profile picture or write-up didn’t initially interest me, my in-person level of interest was no different. For example, I still don’t find tattoo sleeves to be attractive. I just don’t. I tried. Honestly, I did. But there is something (for me) that just doesn’t find that attractive, so why keep pursuing something like that? (Okay, so I’m using a very physical visual example and I’m sorry if I’m offending sleeved or panted individuals. I love your personal form of creative expression, but I can’t help it, I like the the colors of skin, not ink.)

And that naturally leads into the next thing: don’t take anything personally. Just because tats don’t work for me doesn’t mean someone else isn’t drooling over them. And not taking anything personally is more than just this physical representation I keep talking about; it really goes back to non-attachment. I’ve had people not email me back, email me back a month later, email me and then stop (maybe only to email me again later), or even start scheduling dates only to disappear, and to be honest, I’ve done all the same things. It is hard trying to make time in our busy schedules for complete strangers. We really can’t know what is going on with someone else unless they share it with us. So it doesn’t help to fret over why someone didn’t get back to you and this should be easily extended into everyday life. People’s reactions are their own and that is okay. You can’t allow one individual’s reaction control your world.

More importantly, I’ve learned that a lot of lesbians can sometimes be a little too deep for their own good, always thinking about being present and making the world a better place. Seriously, I think it’s great, and I’m so glad that so many women are working in professions that are care-giving and that there are people who give a damn about others. But since I’m being honest, once I hear someone saying “I try to be present everyday in life,” my eyes sorta glaze over and I start to fall asleep. Sure, who doesn’t want to be “real” in this world, but once in awhile don’t we all need a beer and a bad tv show just to check out? And honestly, the things I think about are unmentionable since my parents and sisters might be the only ones reading this blog. Of course I’m overgeneralizing about lezzies, but just ask my colleagues – who have read many of the profiles of the women I’ve dated – and they will agree.

I’ve learned that I can talk to anyone for 2-3 hours provided that there is some type of beverage in front of me – preferably wine, whiskey, or beer. I have never done the proverbial coffee on a date, but once I got tea. Anyway, the point is people like to talk about themselves. I’m not saying that in any rude way, but rather just as truism. (I used to have a good family friend who could get me talking – not that that is too hard – for hours. He just kept asking questions.) First dates aren’t difficult because you are in the “discovery” period, like being in the pre-trial stage of a lawsuit. You are trying to figure out if this case should move forward, end immediately, or if you have no idea of what the next step is.  And that means a lot of questions, which usually build on previous questions if you are paying attention at all. And the truth is that everyone has interesting life stories. But I’ve also learned, while I LOVE to talk, I am really shy about sharing the more intimate things about myself. This is actually a problem because I’m not connecting, but rather leading. And the point is to connect. I’ve been trying to be more open and talk about things I find important or meaningful. It is helpful because how people respond to these things will help me understand what type of partner they could potentially be.

Finally, I’ve learned it takes a certain amount of perseverance to date online. And this is a great life lesson. Getting turned down or ignored can, no matter how hard you try not to take personally, can be difficult on the old ego. But it is a numbers game, you have to expect for every (insert your number here) emails you send out, only 10% will get back. So you gotta just keep getting back on the old proverbial horse (poor horse). Life doesn’t typically just hand us what we want. We have to work for it – we have to earn it.  I’m not saying you have to earn love, I’m just saying you can’t hide from living life and moving forward.

Online dating, whilst I haven’t found a life partner, has helped me partner with my own life in a way that is meaningful. Now, I’ve gotta go send out some emails.

This post was adapted from Rebecca’s original post on her Tumblr, My Life As A Cartoon.

Image:The Raft of the Medusa, by Théodore Géricault (1818)


  1. steph

    So many really wonderful life insights here! Online dating is so concentrated compared to dating in-person. So many people to contact, to reject you, to fantasize about… I’m so impressed that you’ve been able to take such meaningful lessons from such a tough experience– and then written about them with such humor!

  2. “you can’t hide from living life and moving forward” This is a wonderful, candid, and funny piece Rebecca. I feel like, maybe, I’m drinking a Jameson’s on the rocks, sitting across from you in a bar off Guerrero. Now, I’m going to go remove the decorations from the Christmas tree.

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