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Feature

5 dates in 5 nights: Our spies test Grouper, Tinder & more

Our volunteers, Robert Leshner and Rachel Balik, went on five dates in five nights

Singles today have far more options than Match.com, or god forbid, asking out an attractive stranger at a coffee shop. A new crop of dating apps promise to help you find love with a few taps on your smartphone.

With a quick Internet search, you’ll find an array of these new apps ranging from the good, the gimmicky, and the downright bizarre. Which of these apps is right for you? Most of us don’t have the time to sign up for more than one or two of these services, let alone go on any actual dates.

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So VentureBeat asked two brave volunteers to sign up for five online dating services. Over the course of a week, our undercover writers went on a date every single night. Note that some of the first names have been changed to protect the anonymity of their dates — as you might expect, plenty of awkwardness ensued.

You’ll notice that we included few familiar dating apps as well as some relative newcomers, like Grouper and the rather charming-sounding Coffee Meets Bagel.

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Did our volunteers find love in a week? Or were they merely left with a cynical outlook, or worse, dating horror stories? Read on to find out.

Meet our singles

Rachel Balik, 30, is a content marketing manager from San Francisco’s Mission District. Rachel is passionate about coffee, her iPhone, and her MacBook. She pretty much hates dating. Like all true marketers, Rachel can sell anything well — except herself. Share your dating horror stories with her on Twitter @WickedRB.

Robert Leshner, 29, is the founder of Safe Shepherd, a startup that helps you manage your Internet security for free. He also hails from San Francisco’s Mission District. Robert is passionate about economics, civil liberties, and the board game of Monopoly (his personal record is 22 consecutive wins). He enjoys discussing technology with his dates. Ask him out on a date on Twitter @rleshner.

Tinder

Her rating: 2/5
Her review: Plenty of matches, plenty of weirdos 

Getting started: The first thing I realized when I joined Tinder was that I look like an idiot in all my Facebook pictures, so I was forced to log on and do some profile maintenance. While fearing that all my friends thought I was a self-tagging egomaniac, I plunged into Tinder.

OK, “plunged” is the wrong word. In fact, the only way I could get myself to start Tindering was to think of it as a game, which turned out to be a rewarding strategy. In 20 minutes of playing, I was matched with 70 potential dates.

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Unfortunately, I’d say that was the highpoint of my Tinder experience.

Above: David, my Tinder date, invited me to Walmart

The date: As soon as I got my first message asking me if I was “DTF” [which means “Down to F—“] before even saying “hello,” I stopped being interested in dating and launched into a soliloquy about the sad state of young people in America. But when I got a message from David asking me if I wanted to go to Walmart, I was amused enough to reply, “How about Tuesday?”

However, on Tuesday, my coworker mentioned that she received the exact same message from the same guy. Naturally, I made her come with me and we surprised David at Jones Bar with a 2-for-1 deal. We also invited Robert (my VentureBeat co-writer) to balance the ratio. David was totally cool about the surprise — he’s new to town and was psyched to meet new folks in any capacity. It’s not a romantic connection, but David and I are still chatting.

The aftermath: A few days after my date, I received a message from another potential date, Jason, with a poem.

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“Roses are red, violets are blue. I think you’re pretty. Please sit on my face.”

I replied, “Do you think that’s an acceptable way of talking to someone, or are you trying to be offensive?” And then I deleted Tinder.

His rating: 3/5
His review: Good matching feature, but some accounts seemed fake 

Above: A very awkward conversation with a potential date

Getting started: Facebook Connect used to be a “no-no” for dating apps. And now it’s the only option. I connected, and it built my profile. Within seconds, I was swiping left and right to approve and decline matches based exclusively on appearance. Tinder really boiled dating down to its most basic element.

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After judging about 100 potential matches (which took about 5 minutes), I was bored and left the app. And then a funny thing happened. I got a push notification alerting me that I had a match. And then another. And then another. When I returned to Tinder, I couldn’t help but judge another 50 profiles. It was just that easy.

Most of my matches, I realized, were a result of unscrupulous approving — when I viewed their additional pictures, I lost the desire to actually message them. High standards, what can I say.

The date: After a day or two without a worthy match, I started chatting with “Amy,” who looked extremely attractive in her photos. Amy told me that she just got out of the shower and asked if I wanted to webcam-chat with her. Real girls don’t act like this. Having watched Punch Drunk Love, I knew that extortion was just around the corner. I opened the link she sent me in an incognito browser, saw it was a naughty website, and promptly blocked Amy. Spammers are the hallmark of a growing service, so I actually took this positively.

After a few days of intermittent use, I finally connected with Kara. I proposed tacos and margaritas at Tacolicious on Valencia Street (my go to casual date). She suggested a Wednesday lunch instead, and we met up for tacos. She was new to the city and had only used Tinder so far. We didn’t have a romantic connection, but I wasn’t expecting one.

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That night, I got matched with Catherine, and we chatted back and forth through Tinder for an hour. We arranged a date at Local Edition, she gave me her phone number, and then cancelled on me on the day of the date.

>> Turn the page for the next review: Let’s Date >>

Let’s Date

Her rating: 3/5 
Her review: Messy user experience, but it has potential

Signing up: There’s a lot of potential with this app, but it suffers from a messy and often dysfunctional user experience that’s more bewildering than dating itself.

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For example, when you get a match with someone, it loads a calendar so you can set up a date, which is pretty nifty. But when I used this feature, the app got mixed up and sent me push notifications saying, “Mike asked you on a date and you haven’t replied. Let him know either way?” Awkward.

It also suggests matches from far-away places and has a feature that lets you strikethrough what you disliked about a person’s profile but never takes that feedback into account. [Let’s Date recently announced an update that corrects the location problem. –Ed.]

Above: Joe took me to the Latin America Club.

That said, despite frequently wanting to throw my phone at a wall while using it, the app got me plenty of matches. First I chatted with Daniel, who was pretty standard for me: a 29 year-old network engineer at a gaming company. He was too busy to meet up during the week I’d allotted for the experiment, so I decided to move on. I ended up chatting with a 22-year-old investment banker and Joe, a 40-year-old bartender.

The date(s): Amusingly, the 22-year old promised me that despite his age I “wouldn’t be disappointed.” But it would be a bit weird to date someone that young, so I instead I agreed to meet Joe at the Latin America Club. As I suspected, I found it refreshing to talk to someone who didn’t work in my industry.

The one tech related thing we did discuss was how Joe didn’t like Let’s Date, although “it couldn’t be that bad since it led me to you.” (Smooth.)  Although I had fun with Joe, I backtracked on the second date I’d semi-agreed to. I also had to tell the 22-year-old that I’d only been using the app for research. Now that all that’s sorted out, I don’t intend to continue using this app.

His rating: 0/5
His review: A ghost town? I gave up in a week

Getting started: Let’s Date was already installed on my phone from a few months prior. I hadn’t spent more than a few minutes using the app, but I distinctly remember getting a
few connections when I first installed it. For this project, I updated the app to the most recent version and logged in with Facebook (the only option for signing in).

Above: Some of the profiles on Let’s Date appeared to be fake

Theoretically, Let’s Date is a great idea. It’s similar to Tinder, but in addition to pictures, you also see a person’s interests, location, and “tags,” such as “stoner,” “diva,” “brogrammer,” or “Instagrammer.”

You have two choices on each profile, the first being “Let’s Date,” which means you’re interested. When you click the button, you’re asked to “Flirt” (send a message) and move to the front of the recipients message queue, or “Skip.” When you write your message — surprise, surprise — it’s an in-app purchase for $3.99. Thanks for telling me ahead of time. So, on every profile I liked, I hit “Let’s Date” and then “Skip.”

The date — or lack thereof: When you click the ‘No Thanks’ button on a profile, you’re asked to draw a (very
emotionally satisfying) red line through the section of the profile you don’t like, such as their age, location, or pictures.

In practice, Let’sDate is the DMV of dating — but worse, as you’re charged to wait in line.

The interface was an unwieldy maze. The “No Thanks” button didn’t customize my matches — I was expecting that after I drew a red line through Sacramento, Let’sDate would stop showing me potential matches from that city. And after a week of begrudgingly using the app, I had zero (nada, zilch) matches.

I could have been using Let’s Date incorrectly — maybe “Skip” actually skips the profile, leaving only a paid Flirt option as a means of reaching somebody. Maybe the app is a ghost town, abandoned for Tinder and OKCupid. But whatever the reason, I’ve now deleted Let’s Date.

>> Turn the page for the next review: Coffee Meets Bagel >>

Coffee Meets Bagel

Her review: Easy to use, but do matches follow through? 
Her rating: 4/5

Getting started: This app has a few glitches to work out, but overall I’d say it’s pretty brilliant. I had to force myself to open the other apps, but when my Coffee Meets Bagel match arrived in my inbox at noon, my curiosity was piqued, and I was eager to open it. After viewing your date’s profile, you click “like” or “pass.” If you both like each other, you get a text message with an (extremely lame) ice breaker. The message comes from a temporary phone number that is yours to use for a week.

Above: The venue: Upcider in the San Francisco’s Tenderloin District near Union Square.

Image Credit: Upcider SF

The date: I got a match my first day of using the app and immediately asked Jason out. Although I had to make the first move, he suggested a time and location — Upcider on Polk St. We had a very pleasant time, and he seemed like a reasonable match for me on paper. He owned his own web development company, and he’s into running and a world traveler. He was pretty flustered when I came clean about the article, but we managed to bounce back from the awkwardness and enjoyed quality conversation. No real sparks, though.

I also asked him about his experience with the app, and he said he had matches before but never followed through on them. As I continued to use the app, I found that this was a trend, which is kind of bizarre. It means that two people who went through the effort to open an e-mail, click on a profile, evaluate and “like” a person mere minutes before, and don’t bother to follow up when the time comes to send a text. I can see this being a problem for girls who prefer a guy to make the first move.

Would I use it again? I’m still a fan of CMB for its ease and simplicity. And unlike other low-maintenence apps like Tinder and Let’s Date, it does a great job of filtering for people who are actually suited to you, at least on paper.

His rating: 5/5
His review: An easy way to set up quality dates

Above: Success!

Getting started: After connecting with Facebook, Coffee Meets Bagel (CMB) gives you ONE potential match per day, called a “bagel” — delivered via e-mail — which you can “like” or “pass.” The app shows you up to four pictures of the bagel, plus a basic profile as well as a count of how many Facebook friends you have in common.

They’ve invented a virtual currency — “beans” — which you can use to buy features. All of these features seem stupid, except for one-time unlocking the names of your mutual Facebook friends. You might want to use this information before or after a date, if you’re the light-stalking type.

What impressed me most was the quality of their bagels. Having used other services, I was expecting a cross-section of the population. But instead, I almost exclusively received highly educated, professional, attractive women. I’m not sure how their algorithm works, but it’s fantastic. I liked almost all of my bagels. When they Like you back, CMB sets up a disposable phone line for you and your match (similar to Burner), which protects your privacy while making it very easy to coordinate plans.

The date: My first match was Jenny. We texted over the CMB phone line for a few days before meeting up on Sunday night at Tacolicious. She was intelligent and funny, and I would definitely go on a second date with her. My second match was Maureen. We texted over the CMB phone line for a few days before meeting up on Tuesday at Trick Dog for cocktails, followed by Dear Mom to play Ping-Pong. I would definitely go on a second date with her.

If you’re seeing a pattern, reader, so am I — CMB is an easy way to set up quality dates.

>> Turn the page for the next review: Grouper >>

Grouper

Her rating: 3/5
Her review: Easy set-up, but it all went a bit haywire 

Above: My “wing women” — I owe them a strong drink.

Getting started: Grouper is great because it’s basically a concierge service for dating. They schedule a date for you, pick a location, and send you friendly e-mail and text messages to make sure everything goes well. To set up a Grouper, one person, the “leader,” fills out a quick questionnaire to determine appropriate matches and then waits to hear about an availability. (The current waiting list is four weeks.)

The date: I recruited two wingwomen, Lauren and Amy, who both asked for some idea of what to expect.  As it turned out, even if I could have told them, we still would have been surprised. After I interrupted our perfectly pleasant, laughter-filled date to explain that I’d be writing about it for VentureBeat, the guys replied that they too had a secret.

Apparently the actual Grouper leader, John, had a girlfriend. When she found out that he was doing Grouper, she (naturally) freaked out and put a stop to it. At the last minute, he convinced his friend Nick to take over his Grouper. The only problem is that Nick, in his words, “isn’t exactly straight” and his friend, Akshay, is tentatively betrothed to a woman in India. The third guy, Remy, who barely seemed to know the other two, had been coerced into going and was a bit resentful, caustic even. (He told me I seemed like the kind of girl who was going to die alone.)

The aftermath: This night was incredibly fun in an absurd sense. It definitely will be a story I tell my brother’s future kids when I become an old, crazy aunt. Given how haywire it went, I’d be hesitant to pay $22 to go on a Grouper date again; meeting eccentric guys with zero dating potential is something I do very well on my own.

His rating: 3/5
His review: It didn’t quite live up to the hype 

Getting started: I was most excited to try Grouper. The startup has built a tremendous amount of hype by restricting access and sharing “groupergrams” of people having a wild time on their dates; one picture shows some fellas holding up their dates’ underwear. But in the words of Public Enemy, “Don’t believe the hype.”

Above: Grouper was a good excuse to get my guy friends out on a weeknight

Upon joining Grouper, my dating concierge, Challen, set up a Grouper date with three girls, a few days in the future, location to be determined. I recruited two wingmen (both Safe Shepherd colleagues, Reid Cuming and James Slingerland). We filled out our profiles, and the day prior, received our location, Asiento. I had never been to Asiento before, even though it’s in my neighborhood.

Their party showed up on time, we had two rounds of drinks and appetizers, had a lot of fun, and decided to call it a night — they had to get back to the East Bay. At this point we revealed that James, my wingman, was gay, which they couldn’t believe. A fun night, and in Grouper’s favor, “not our usual Thursday.”

I decided to try again, and organized another Grouper date. This time, my concierge picked Dear Mom, one of my favorite bars. I picked Noah Sidman-Gale, a self proclaimed “bro,” and Eric Shen, who just moved to the city, as my wingmen — an eclectic party. Their party showed up on time, and things started off on the right track. An hour in, the momentum slowed, so Eric invited his backup-date to the bar. And then the Grouper dissolved into animosity. One of the girls revealed that she was in a relationship and not looking to meet anybody, and the other two decided that it was ice cream and parting time. Our bartender, the Grouper coordinator, explained that we did better than most Groupers he’d seen — the supermajority, he explained, end quickly and awkwardly after one round of drinks.

Everyone I’ve spoken to about Grouper (and most of my dates during this experiment) have had similar experiences. I’m not a dating statistician, but the odds of any two people liking each other are low; the odds of three pairs of people hitting it off seems orders of magnitude lower. I have many friends interested in trying Grouper, and I wouldn’t be surprised if they convert their hype into a large funding round, but one built on a broken premise. I would try Grouper again — but only to get two friends out of the house on a weeknight.

>> Our final dating service may surprise you >>

The old fashioned way

Her rating: 5/5
Her review:
Better than any dating app

Above: Scott didn’t have a beard as promised.

We decided that the best control group for our experiment would be to ask someone out in real life. The good ol’ setup by a friend is the original dating app, so I turned to my partner in crime, Robert. He assured me his friend Scott was tall, very smart but socially adept, athletic, and to top it all off, has a nice beard (in theory, my type). Imbued with that minimal information, I ended up on a date with Scott about an hour after he first texted me.

Scott didn’t actually have a beard when he showed up, but he was polite and easy to talk to. I agreed to a second date in exchange for permission to write about him for this article, but it hasn’t happened yet.

Robert also sent me up with another friend, Chris, who I definitely clicked with when we met at happy hour.  We ended up at a concert together accidentally the next night, but my burnout from this experiment left me more committed to my new, viral blog idea: “40 Days of Not Dating.”

Despite my newfound antisocial tendencies, I have to say that meeting in real life is better than any dating app — more specifically, having a lot of friends who can expand your social circle. After this week, I feel more strongly than ever that dating is an unnatural activity.  If there was an app that let you get to know lots of people in a nonromantic, casual way, I might consider using that. That is, if I ever decide to leave my room again. …

His rating: 4/5 Stars
His review: I got burned, but I’d still go the old-fashioned route 

Above: Fatigued by dating apps, Robert ditched his phone in favor of a good-old fashioned setup.

As a baseline, and point of comparison, I tried going the “normal route” during this project – meeting people offline, but without making any special effort by which I’d bias my research.

I met a nice, interesting woman at a party, who also worked in technology, and got her phone number. But I didn’t set up a date — I was busy enough with five nights of dates from dating apps for this story. I also met a woman at Lone Palm (one of my favorite local bars), who I would be interested in calling. And I had dinner with one of Rachel’s colleagues, Lauren, who declined my offer to go out again. (Burn!)

After all of this, I still prefer meeting people the old-fashioned way — in real life.

Editors’ note: Rachel and Robert are now fast friends. Neither found love through this experience.