Online Dating

Twelve years after Markus Frind founded PlentyofFish as a side project, the company sold to Match Group for $575 million. That's an impressive price for anyone, but it becomes astonishing when you consider the site's origins.

Frind launched POF from his apartment and, for the first six years, didn't hire any employees or raise a cent of venture capital. That would be bad news for any other company, but Plentyoffish.com was already getting 2.2 billion page views a month and generating millions of dollars in revenue.

The risky move turned out to be a brilliant one. Except for the IRS, Frind didn't have to share the funds with anyone. He had money to continue his business, travel the world, and buy anything he could imagine. Match tried to purchase the company for a decade, and Frind could easily say no.

He continued to grow POF on his own. At the outset there was no advertising budget, no business plan, and only a basic website. Frind's experience was practically non-existent, so he taught himself about marketing, business development and product. It wasn't until 2009 that he hired his first developer – and he was still running the business out of his apartment at the time. It didn't matter. By then, he had 10 million users. To say it happened “against all odds” is almost corny.

Frind's perspective changed last year, when his daughter Ava was born. “Having a 10-month old daughter, you start measuring time in different increments,” he said in an interview. “Every day you see something’s different – she’s trying to take her first step, or she’s crawling around. Whereas before you measured the company in milestones in terms of the revenue or user growth or some kind of company target.”

Now, having sold his miracle online dating company to rival Match Group, Frind is contemplating the future. He says he has already bought everything he could personally want, so many hope he will instead use his wealth invest in the startup scene in his hometown of Vancouver.

“I think he will invest a lot more and help a lot of businesses,” said Arash Fasihi, founder of online furniture retailer Cymax Stores Inc., to The Globe and Mail. Fasihi's company recently received an $18 million investment from Frind and made him a director.

Vancouver venture capitalist Boris Wertz has similarly high hopes: “He’s a smart guy and he knows how to deploy money, and hopefully some of that will flow back into the tech ecosystem.”

For more information on Frind's dating site your can read our Plenty of Fish review.

When I talk to daters, the majority of them have tried online dating and decided it just “doesn’t work” for them. I understand – we have all been through some bad and good online dates, and sometimes when you have a string of disappointments it’s enough to make you want to give it up altogether.

Here’s why you shouldn’t.

I’ve heard the arguments about how dating and meeting people should be more organic, that people on online dating sites are just looking to hook up, that it’s hard to know who you are really meeting when you get to the date because your dates don’t look like their photos. All of this happens from time to time. But it’s also important to remember one basic and compelling fact: online dating makes meeting people much easier than approaching strangers at the grocery store, for instance.

Online dating is really a misnomer: it should be called online meeting, as Dr. Helen Fisher of Match.com once pointed out. It is an avenue of introduction, but it is only that: an introduction. There’s no guarantee of love at first sight, that you will have the same goals, that you have a similar sense of humor, that there will be chemistry. But you will have people to choose from, who have chosen to take part on the site, and to date (as opposed to that random stranger at Starbucks who might already be in a relationship).

We have become products of the online dating generation, which makes actual dating more difficult. We expect to know as much as possible about someone up front before we agree to spend time together, even if it is just over coffee for twenty minutes. We approach dates with caution and skepticism. We shut down if there isn’t that instant spark of chemistry, instead of trying to get to know someone past the awkwardness of a first date.

Most importantly, we’ve come to expect that there is always someone “better” out there, waiting to meet us. Daters tend to prefer to keep swiping on Tinder even after they have met someone who sparks their interest, because maybe – just maybe – that next person will be even better. So we’re never in the moment – we just anticipate meeting the next person, and then the next. This is killing dating.

In order to feel chemistry, to connect with someone, you have to be present in the moment. You have to be fully engaged. Otherwise, the connection simmers, and perhaps you both walk away feeling “meh.” Then it’s on to the next – and that person might have really been a good match. You just didn’t give him/ her enough of a chance.

So on your next date, take your time. Engage. Try to be fully present. Put away your phone. Talk. Ask questions. Listen. Then see how online dating works for you.

Cheaters are having a bad week.

In case you're not up to speed on the latest scandal to rock the online dating world, here's the gist: a group of hackers calling themselves The Impact Team attacked Ashley Madison and gained access to the site's database of 37 million members. The hackers got hold of financial records, addresses, and other highly sensitive personal information, and have threated to publish it online unless Ashley Madison shuts down.

Avid Life Media, Ashley Madison's parent company, says it has secured its sites and is working with law enforcement agencies to find the parties responsible. Despite their efforts, files containing emails and passwords for some Ashley Madison users have started to spread online.

Some have called this the beginning of the end for Ashley Madison. It's devastating for any website to be hacked, but infinitely more so when it's designed for a philandering clientele whose top priority is privacy. Ashley Madison has failed to uphold one of its most important – perhaps the most important – promises.

And it gets worse. Avid Life Media announced earlier this year that it hopes to raise $200 million in an initial public offering in London in 2015. The brand's value is based almost completely on the service's ability to protect its members' privacy. Without that, is the Ashley Madison worth anything in the first place?

“If a password manager such as LastPass was hacked,” writes Christina Warren for Mashable, “the service would be dead in the water. After all, the whole point of a password management service is to secure and protect your passwords.”

The same principle applies here. Ashley Madison's adulterous target audience is likely to be wary of a site with a history of being hacked. New customers will think twice before joining. Current customers will jump ship. And the IPO? If the hack doesn't squash it completely, it will at least significantly reduce the value of the company.

A renaissance isn't impossible. Other companies have endured disasters, rebranded, and risen from the ashes. It's possible that Ashley Madison could update its security practices, change its name, and come back to reclaim its place in the online dating market.

But should it? Will anyone buy into the narrative that Ashley Madison has seen the error of its ways and reformed? Will cheaters, who require privacy more than anything else, take a chance on a service with such a shoddy track record? The damage may already be irreversible.

Late last year, a lawsuit was discreetly filed by Spark’s popular niche dating website JDate against dating app JSwipe. According to Forbes who broke the story, JDate claimed that JSwipe was infringing on the company’s trademark “J” by using it in the name of their app.

JDate isn’t the only Jewish online dating website that caters to the Jewish community and uses the letter “J” in its offerings. There is also JCrush, JWed, JPeopleMeet, Jewish Café, and Jewcier to name a few. In fact, it seems difficult to name a niche dating app catering to the Jewish community without using the letter J. But there is more to the story, which potentially puts all online dating sites and apps in danger of patent infringement.

In the lawsuit, JDate also claims it owns the patent on software that “confidentially determines matches and notifies users of mutual matches in feelings and interests.” JSwipe is similar in its process to Tinder, which also notifies users when matches swipe right on their picture. This is in violation of JDate’s patent.

Why then has JDate not sued other websites or dating apps, since this is such a broad definition of matching that almost every dating app and website uses? Notifying users of potential matches is the bread and butter of online dating. Why not go after an app like Tinder?

The key might lie in the competition JSwipe presents, especially if it is gaining market share in the niche online dating space. According to the Forbes writer who broke the story, JSwipe’s founder David Yarus confidentially confessed the lawsuit to him, though he is forbidden from discussing details. Instead of accepting JDate’s acquisition offer (which he considered too low), he decided to fight the lawsuit rather than sell. (For all you fans of Silicon Valley on HBO, this sounds vaguely similar to Pied Piper’s plight as an up-and-comer in the tech world.)

But JDate might have a case against JSwipe. According to Forbe’s research into intellectual property law, the language used in JDate’s patent was registered in 1999, and it is broad – broad enough (as mentioned earlier) to cover most dating websites and apps on the market today – so they could essentially claim IP infringement over any other company in the space. According to analysts, this might be a move by JDate to acquire JSwipe for a steal. Chances are if they tried to sue Match or Tinder, those companies' lawyers would be able to fight and win. JSwipe is too small a player.

Using the letter “J” in a dating app or website is apparently less clear-cut in legal terms. JDate would have to find evidence that users confuse Jswipe with JDate, which means asking users to testify that they thought Jswipe was part of JDate, or somehow affiliated, which would be trickier and more time-consuming.

JSwipe is fighting back. They have set up a crowdfunding website and asked for Jewish lawyers to take them on pro bono. 

For more on the Spark Networks dating site, you can read our review of JDate.

You've heard that you need to put your best foot forward online. So, thinking you were doing exactly what you're supposed to do, you agonized over your username, your self-description, your photos. Every detail of your profile was carefully reviewed and redone until you felt confident you'd achieved perfection.

What if all of that was unnecessary? According to research from the University of Iowa, appearing too perfect online can actually work against you.

The study found that daters are distrusting of profiles that are too flashy or flawless. Instead, the most successful profiles are those that offer an authentic look at who a person really is.

"We found people want to contact a person who appears to be accurate in what they are saying about themselves online," said one of the study's authors, University of Iowa communications professor Andy High, in a statement. "It's tough when it comes to dating profiles because we want someone who seems like an amazing person, but we also hopefully will have a relationship with this individual, so we want them to exist."

To test how daters respond to different types of dating profiles, the researchers created 8 fake OkCupid profiles (4 men and 4 women) with combinations of two possible orientations. The first was “Selective Self-Preservation.” Profiles with this orientation highlighted the good aspects of the person's life while downplaying the negatives. The other kind of profile, “Warranting,” contained information that could easily be traced to a real person.

150 men and 167 women were asked to review the profiles and decide which ones they would contact. The majority chose profiles of the second type – those that did not present the person as perfect, and contained info that made the person feel more real.

In other words, people were turned off by profiles that appeared too good to be true. When stories of online love gone wrong come out on a daily basis, it's hard to blame them for being wary.

“Users of online dating sites are aware that people misrepresent themselves, and inaccurate profiles are one of the biggest drawbacks to using online dating sites,” the study says.

It's a difficult position to be in. Paint an unattractive picture of yourself and your profile won't get very far. Paint a picture that's too attractive and you're in the same boat. So what's an online dater to do?

“You want to balance all that is wonderful about yourself with some things that aren’t negative, but more humble or realistic about yourself,” says High. “It’s important to put your best foot forward, but maybe not in your best pair of shoes.”

OkCupid has built a strong reputation for taking a more progressive approach to online dating. Back in 2014, the company began offering users more options for self-identification. Gender was expanded to include agender, androgynous, genderfluid, intersex, and more. Choices for sexual orientation were also extended, including asexual, pansexual, queer, and questioning.

Now OkCupid is continuing its efforts for more inclusive representation. The company recently launched a new project called 'Identity' to encourage conversation about sexual orientation and gender identity.

“When OkCupid expanded the available gender and orientation options,” reads the Identity website, “we realized there was a larger conversation taking place. Because dictionary definitions aren’t always able to tell a story, we went to real people to add some color to this evolving language. Here are descriptions from those who claim these words for themselves.”