In our fourth installment of our “Coolest Apps” blog series, I spoke with co-founder Kevin Murray about his app, Icebrkr.

When my friend and I (we did it together because my friend has a boyfriend and wanted to live her single life vicariously through me) made a Bumble profile in July, she had a few steadfast requirements:

“No, don’t put a picture of you in a group…you can’t figure out who is who.”

“No, don’t put that picture of you and your brother… he could be your boyfriend, it’s confusing.”

“Stop! Don’t put that in your profile–you have to say something clever, original, but also controversial. How about, Will order a pink Cosmo at a dive bar.” (I’ve never had a pink Cosmo, but when I said this to her, she said, “It’s a joke. He’ll get it.” He being, well, everyone).

This is all before we started trying to talk to these boys, which, well, forget it. “Heyy,” never worked, although, “Happy Tuesday!” had a slightly higher response-rate. I was already tired of wasting my energy coming up with anything clever, so my friend took over, checking out his profile to say things like, “If you took me fishing I bet I could catch a bigger fish than that,” or something equally odd-and-potentially-offensive, and this, we quickly learned, worked best. Still, the conversations never went that far from there.

When I sat down to speak with Kevin, he mentioned something interesting. “You know, when you ask people to think of search engines, they usually say only one: Google. But when you ask them what dating sites they’re on, they usually give you about five different answers… [because] no one’s quite nailed it yet.”

So what do you do when you don’t have a friend like mine, willing to grab your phone out of your hands to do the creative-message-crafting for you? Or, more importantly, what do you do when you do have those friends… but they aren’t any better at it than you are?

Kevin believes his app can solve that. Icebrkr is a dating app with a personal dating-coach, in the form of an owl named Hootie, “who is, essentially, your wingman… no pun intended,” Kevin explains. Hootie gives you personalized recommendations and advice regarding how to build an accurate, compelling profile, which photos to add, and even what to say when you start messaging someone–how to break the ice, and all that.

Kevin’s background in online-dating is impressive–as best he could, he essentially majored in online-dating, and he also has his own personal experience to glean from. He online dated on-and-off for 10 years, and when he went to grad school, he gathered as much information about online-dating and relationships as he could, even taking body-language classes to learn about courtship. (Mark Brehaut, his co-founder, studied relationships as well, with the goal of becoming a marriage and family counselor.)

Kevin thinks his experience sets Icebrkr apart: “I use all of my academic background… So everything [is] grounded in communication theory, and I’ve yet to see a site that [uses] a lot of those resources.”

After finishing school, Kevin landed a position at eFlirt. By the end of his two-and-a-half years there, Kevin was helping run people’s online dating profiles from all across the country. They were paying $16,000 for a four-month commitment. He was learning that people are willing to pay big for dating advice–discreetly.

“Some people are embarrassed that they have to ask for help. I don’t get it… I mean, who cares? There’s just so many coaches in other aspects of life, I don’t get why people think they’d be looked down upon [for needing dating advice].” He hopes Icebrkr will “reduce uncertainty and raise confidence.”

After tentatively drawing out a design for what would become Icebrkr, Kevin decided to quit eFlirt because, “Even though Icebrkr was a couple of shitty drawings, stick-figures on pieces of paper, I was betting on myself.”

Not that it has been easy. Although they’ve raised $50,000 already, mainly from friends and family, Kevin explains it’s been hard to show investors the app will gain traction–without having the money to create the app in the first place.

In the meantime, Mark came up with the idea to create an SMS system. Right now, you can sign up to text a Google number (text promo code ‘break the ice’ to 347-796-1643 for 5-days free) your online-dating questions and Kevin himself will answer them.

So who are they targeting? If you’re die-hard Tinder for all the reasons most people are die-hard Tinder, this probably isn’t for you. “We’re targeting 24-44 year olds, looking for something more serious.”

When we get on the topic of Bumble, Kevin describes it this way: “Bumble is basically the ‘Yellow Tinder.’ They’ve done a good job of branding themselves as more serious, but fundamentally, it’s the same [as Tinder]–you know, six pictures, a cliche movie quote, and a pizza emoji… There’s nothing earth-shattering with what these sites are doing.” He has a fair point; although many of my friends have graduated from Tinder to Bumble in the hopes of appearing more “serious,” both apps mainly encourage quick, superficial messages, and late-night invites to watch The Office.

So why Boston? Kevin explains that they plan on starting in Boston because they have to start in one area and that’s where most of their connections are–but they hope to spread quickly.

The biggest challenge for them, Kevin tells me, is “basically just the challenge of, how bad do you want this? You can’t be in a rush for it to happen.”

Seeing as they’ve been working at it for 2-years now, and Kevin is sacrificing his own time (mainly the hours of 9 p.m. to 11 p.m., when it’s most popular), to mechanically answer people’s online-dating questions via text, my guess is… they want this pretty bad.

I’m personally hopeful that this can redirect why people join online-dating apps in the first place. There’s certainly a big discrepancy between Tinder and Match.com, and for people who fall anywhere in the middle, a major gap in the market.

Plus, unlike all the other dating apps, this one provides Hootie, who, unlike my unnamed friend from the beginning of this article, might actually know what it’s talking about (the owl is, I believe, gender-neutral).

**Have a suggestion for another app/inventor to be featured in this series? Comment below!