Millenials Guide to Online Dating


Picture a twenty something single living in the depths of Brooklyns. With hour commutes to work, and having no luck meeting that special someone in a social scene of silent movie festivals at the Film Forum, my lovely lady-friend Lisa joined the fleets of Millenials trying to find love—online, for free—on the dating website Ok Cupid.

To her chagrin she found love—after two attempts with the website—and one night sipping cocktails out and about a trendy bar scene she shared the nitty gritty of finally getting it right.

What she realized was dating online was exhausting. You have to recreate at the best of your ability the charismatic personality all family and friends know and love—except to a zillion strangers online. After completing a profile and uploading the best selfies one can find from an Instagram feed, you then have to answer countless questions asking moral, political, and ethical questions meant to connect one to matches with similar world views.

This was Lisa’s second attempt on the website. Her first go-around only led to dizzying circles of self-contempt and confusion. Most Ok Cupid-ers were serial daters only wanting a night of fun, while my friend was looking for a long term relationship. Her disgruntled first attempt led to a brief three month hiatus from the website. With summer in the air she was ready for another go,  and she started fresh with a new online profile and a devout agenda of complete honesty. Her new strategy was to be herself—online—and it paid off. After only a few months she met a great man who is now her loving boyfriend.

Interested in learning how Lisa nabbed the partner of her dreams? Here are the secret tips for her success:

Be yourself. Online.

If you have read Ok Cupid profiles you would think everybody is Louis CK guest starring on the Office discussing their middlebrow love for The Hunger Games and J.D. Salinger’s Catcher in the Rye. We are all the next Lena Dunham when it comes to our status updates, but it is important to project yourself, online. Lisa wear glasses, a ton of faux fur, and reads more Art Criticism than your average NYU student, but is far from being an ironic scenester. She’s an aggressive conversationalist, and on the first date with her now boyfriend, chit chat quickly became a discussion on Marxism and art. Later on he told her after their first date, he re-read her profile and thought, “Yes, this is her.” Hiding behind a facade may only misguide and stall meeting potential matches.

Message Less. Meet more.

Lisa learned this through trial and error. She invested time and energy into a very detailed back-and-forth with an early thirties programmer living in Williamsburg, Brooklyn. It was a match made online. They both loved Vittorio de Sica more than Fellini, shared a passion for Japanese Ramen, and had just visited the public art museum Storm King. All points were bells to any art enthusiasts ears. She became connected to his internet persona and had high hopes for their dating potential. They went on one date, played Jenga by fireside at a Williamsburg beer hall while he showed her photos of his recent paintings on his iPhone. Much to her chagrin, he never called her back.

On the flip side, her now boyfriend messaged her on Ok Cupid a week later, “hey do you want to meet up sometime?” and her response was, “Yes.” And scene. Spending too much time sending Shakespearean soliloquies back and forth in an attempt to get to know someone before an in-person commitment is like throwing dust in the wind.

Dating is difficult, especially in New York City, let alone the vortex of Ok Cupid and the influx of emails from serial daters and party people. Call it luck, coincidence, or being online at the right time, Lisa found her boyfriend because she laid it out online from the beginning.



  1. psychosomaticallyinlove · March 22, 2014

    Lovely read, thank you! Applies not only to millenials, believe me! 🙂

  2. Al · March 25, 2014

    Thank you 🙂 Mine was another go after finding someone on a different dating site last year who was not completely honest with me. Okay, she was completely dishonest with me. From her name, to her relationship status and even finding out that she was pregnant. Which is why I thought I would give it a go now. Only to end up with the one you read on my blog.

    Thank you for the link back 🙂

  3. girlwithadragonflytattoo · March 25, 2014

    I love this! If there’s something I absolutely love about our millennial gen Y’s is the honesty and openness… I’ve met more Gen Y’s than any other generation that are absolutely honest and forthcoming and it’s just so refreshing. 🙂

    • Becoming Middlebrow · March 26, 2014

      Thanks for your thoughts! Your words are much appreciated, I look forward to reading your future articles!

  4. masterbeta7777 · March 25, 2014

    Hey man! Thanks for reading my article on Ok Cupid Dating and Sex:

    And thanks for referring me to your site. I do agree with what you’re saying, especially with “Message Less. Meet more.” I am specifically scribing my articles with the perspective of a prospective player; with the eye of an Alpha male in the making. And that’s when getting the number quickly comes in handy. People lose interest, especially when they’re talking to strangers they only know online. In a sense, retrieving the number quickly and moving on to in-person conversation will be defined as “classy” by the guy or girl of interest. Stay in touch.

  5. singledate1 · March 26, 2014

    Lovely ending … superb read, thanks for sharing ..

  6. Dating Ann · March 26, 2014

    Loving every bit of it! Thanks for reading my blog as well 🙂 You just made me want to join OkCupid and I already have a boyfriend lol. I live in Brooklyn too by the way 🙂

  7. CarissaMarie · March 26, 2014

    Online dating never ended well for me. I was completely honest, but trouble was, most weren’t honest with me. I, all too often, ran into either people looking for “fun” or people that resembled stalkers too closely. A few times, we just agreed we were only friends material and that was okay, love making friends. But yeah, in the end online dating wasn’t for me. It does work for some, as is the case for your lovely friend and I so happy she found someone who makes her happy in this crazy messed up world!

    My friend, Gina, was using E-Harmony and at first wasn’t having any luck herself. But, her last match turned out to be the one. He is from England and her from the lovely frozen tundra, otherwise known as Wisconsin….though was living in Colorado, working on her graduate degree. So, they talked online and over the phone for awhile, but then did eventually meet. They married in April of 2010 and she moved to England at the end of May that year. Fast forward four years and now they also have a little family of their own. She is only one of a few that I personally know who has had real success in the world of online dating. I know it can happen. It just didn’t for me.

    I found my love through mutual friends. And believe me when I say, I have also had some bad experiences when friends have tried to set me up with someone they say is “perfect” for me. But, this time, the constant talk about our friend Doug led to something. Though, we came to it apart from our friends. We didn’t want them involved in the “getting to know one another” stage. We wanted to find out for ourselves if we would be a good match. We became friends first, just talked, hung out, and really got to know one another.

    One point I will agree on with your post and it is the same no matter how you search for your match….BE HONEST! We laid our cards out on the table from the beginning, saves a lot of time for both parties, ya know? I have spent my fair share of time chasing love, pursuing the “wrong” ones. I was done beating around the bush and while he’d only had one girlfriend prior to me, he had been put through the ringer and was not about to go through that again. Well, sufficed to say, here we are, five months from being two years since we began talking and we’ve been together for what will be a year and a half April 16th. We have been living together for what will be a year on May 23rd, my mom’s birthday oddly enough. We’ve been talking marriage and we both know that’s where we’ll end up within the next year….married, though we live like we are now ha ha, but we do want to make honest people who love God out of one another. 😉

    I say no matter where you look….online, personal ads in the paper, going to public dating sessions, through mutual friends, going out to the clubs, maybe even meeting at church, or wherever you might look….be yourself, be honest, and if it’s in the cards for you, it will work out. If it feels forced, don’t waste your time. It should feel natural. Love is a natural emotion, not something you have to make yourself feel. But, to all the skeptics out there, it is real….just have to know it when you see it. Listen to your heart, but don’t forget to also listen to your mind. When they work together, wondrous things can happen. I loved reading this and thank you for stopping by and reading my post about love as well!

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