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Dating...There's an App For That


I first entered the world of online dating as a nineteen year old. Ten years ago, online dating was highly stigmatized and seen as a cry for help. I am proud to call myself an early adopter. I’ve been a member of at three separate ages (19, ~25, and ~28). The online dating landscape has changed significantly over the past decade. More players are moving into mobile app platforms. We do everything else on the move, so why not find your next date that way as well? I’d like to share with you my perspective on several different services. I’ve gone on dates through four of them (OkCupid, HowAboutWe, and eHarmony) and have joined the rest to form an opinion. 


Category: Sites That Have Led to Dates


OkCupid (

Positioning: “Join the best free dating site on Earth. Start meeting people now!”

Reality: The Fastest Way to Hookup 

Cost: Free (Upgrade to A-List, 1 Month Contract: $19.95 per month to 6 Month Contract: $9.95 per month)

Guarantee: None. I do guarantee that you will hate how much you love it.

Some of the Most Ridiculous Questions You Can Answer on the Site:

  1. Have You Ever Hired a Prostitute for Yourself? [Note: I appreciate the specificity of “yourself” and not “your friend”]

  2. While in the middle of the best lovemaking of your life, if your lover asked you to squeal like a dolphin, would you? [Note: If is name is Flipper, you were warned!]

  3. How do you eat your cupcake?

  4. Would you consider dating someone with a glass eye? [Note: Depends on how he eats a cupcake]

Personalitini Score: 4/5

Although this site markets itself as free, you can upgrade your account to A-List. I tried the free version for several months and got frustrated, so I forked over nearly $60 for a 6 Month Trial. For a cost significantly lower than most other sites, you are given multiple features. My two favorites are invisible browsing (you can stalk your new crush without him knowing the depth of your obsession) and seeing which members have rated you as a 4/5 or 5/5. These two features eliminate a lot of the wasted time on the site; I can focus on people I’m interested in that are ALREADY interested in me without scaring them by my profile views. Win/Win.

“Best” Dating Story: Oh my. Where to start? Through all of my online dating experience, the dates I’ve been on through this site FAR exceed all of the others. Some of the best stories are a bit too aggressive to print, so I will offer a takeaway: I’ve had some of the best dates with people I had a fairly low match %. OKCupid matches you with other users based off of % Match/Friend/Enemy. I’ve gone out with people I had 99% Match Compatibility that were truly terrible and people that were 50% Enemy that were a delight. It just goes to show that chemistry is far more complicated than a computer algorithm.


HowAboutWe (

Positioning: “Join Free & Post a Date Idea. Start with the words, “How about we…” then suggest a date you’d like to go on”

Reality: The Site Where the answer to “How about we…” is always “get cheap drinks at a shitty bar”

Cost: If you want to interact, you gotta pay! 1 Month Contract: $34.99 per month to 1 Year Contract: $7.99 per month

Guarantee: “The 100% Get-Offline Guarantee” – basically only covers that you’ll meet a real person on a date…woo hoo!

Posted Dates by Actual Users: How about we…

…have brunch at the Central Park Boat house followed by a leisurely walk in the sun.

…take a plane to London for a spontaneous long weekend.

…go skydiving – it’s been almost three years since I last went.

Personalitini Score: 2/5

I went on a handful of dates that were not awful. That being said, the incredible date idea posted by the date in question WITHOUT FAIL never ended up being the date he suggested. As a silly dater, I assumed that the premise of the site was to go out with someone on the posted dates. Apparently, they are just window dressing to entice someone. Ultimately, however, you do feel the unfortunate beneficiary of a “bait and switch” when that swanky bar he suggested ends up being The Four-Faced Liar.

“Best” Dating Story: I bring up that West Village Bar because my first HowAboutWe date took place here and not at the uber-nice bar he suggested we check out. When I arrived, I noticed he was sitting very close to some random dude. After I met him, he kept saying, “Who is this weirdo that is sitting so close to us?” I tried to see the silver lining of this date with each sip of warm beer. It turned out that the “weirdo” was actually his friend that he brought to join him on our date. This is by far the closest I’ve ever gotten to a threesome. (

Positioning: “ has led to more dates, relationships and marriages than any other site”

Reality: Pay for the same experience you get from OKCupid 

Cost: Don’t post rates unless you provide a username and start a “Free Trial” – I looked at my renewal rates: 3 Month Contract (minimum): $26.99 per month to 1 Year Contract: $20.99 per month.  

Guarantee: If you sign-up for a 6 Month Contract and you don’t find “someone special” within 6 Months, you get 6 additional Months Free (so not a refund exactly…)

Unique Usernames:





Personalitini Score: 2/5

Since you can only interact with users if you pay, there are limited benefits to this site unless you’re a member. The argument for paying to communicate with other members is to place a hurdle to filter out people that “aren’t looking for a relationship.” Call me crazy, but if you’re paying $0 for OkCupid it does not mean you don’t want a relationship; the same logic follows that paying $30 for a service does not mean you’re not just looking for sex. Before moving to NYC, I had really great success with in Charlotte. When I moved here, it was the first service I tried. I was surprised that I had such a different experience; maybe it was market dynamics! I joined OKCupid and found that I was having much better success (for free!) than on I didn’t renew my subscription. Based on that, my advice is to try out a couple different sites to see what works best for you! Just because you save money, don’t lock yourself into an annual contract right away.

 “Best” Dating Story:

When I was in Charlotte, a date sent a limo to pick me up to go to dinner at an upscale restaurant in Charlotte (Bentley’s Restaurant, if you’re familiar with the area). Initially, I was hesitant. What if this limo was taking me to my imminent death and not a decadent meal? Armed with pepper spray (I would likely injure myself with it first), I got into the limo. During the date, he casually mentioned he was a widower. This nugget was not the appetizer I thought I ordered. I also made a faux pas by ordering my own food. Apparently, we live in the Stone Age and I was supposed to tell him what I wanted so he could tell the waiter: he wanted to play dinner telephone. Did I mention he somehow found out where I worked and sent me an Edible Arrangement? [Note to the Men: if you really want to charm a lady, send her fruit on spikes in a cup. Nothing gets her more pumped than that.] The best part of the date was the walk home. I felt that if I got in the limo it could have ended up like the Bone Collector.


eHarmony (

Positioning: “Beat the odds, Bet on Love with eHarmony”

Reality: Pay to be matched with people that you do not find physically attractive but are great on paper! 

Cost: 3 Month Contract: $39.99 per month to 1 Year Contract: $19.65 per month

Guarantee: The Premier Package – if you’re unhappy during your 1 Year Contract, you can add an additional year for free (this “package” costs $41.95 per month!)

Personalitini Score: 1/5

I really bought into the marketing. Dr. Neil Clark Warren (the old white guy in the commercials) really nailed it. I just had to fill out a never-ending survey and they would do all the work! Each day, I would be served up potential soul mates! HOW FUN! Guess again. Without the ability to search through the database, you’re at the mercy of an algorithm. Shockingly, just because you both love puppies, brunch and live in the same city does not mean you will want to make out with each other.

 “Best” Dating Story

After continuously rejecting my “hand-picked” matches, I finally found someone I was physically attracted to that was also attracted to me! We scheduled a date and met up. At the end of our date, I asked him what he was up to later that week.  He started chuckling and shared, “I’m going on a date with your friend that is in your eHarmony photo.” Watch out Romeo! Rico Suave here was also matched with my close friend that was on eHarmony and figured out we knew each other by our uploaded photos. Genius Alert! I don’t know if he thought this would be a strategy to go out with both of us at the same time, but I was over it after that. It hit too close to home. #TMI


Category: Honorable Mentions


Hinge (

Positioning: “Make a Real Connection”

Reality: Have Peace Knowing that that Guy Not Interested in You Knows 5 of Your Facebook Friends


Coffee Meets Bagel (

Positioning: “Quality Dating Made Easy”

Reality: “This sexual analogy is confusing. Who is the bagel?” (An elegant argument brought to my attention by Christine)


Tinder (

Positioning: “Tinder is how people meet. It’s like real life, but better.”

Reality: Tinder is how people hook up. It’s like porn, but real.


As always, I’d love to hear your perspective! Which site has given you the best results? If you’re thinking of taking the plunge into online dating, did my advice help? I hope so! Tweet me @personalitini!