Dating service industry is expected to grow another 4.2% in the next five years. Bela GandhiBela Gandhi, founder of the Smart Dating Academy in ChicagoDeciphering the meaning of a winky-face emoji is a job for professionals. Enter the love entrepreneurs. The love guru business is nothing new—matchmakers have been around for centuries. But demand for dating services is growing, and movies like Hitch and the reality TV show The Millionaire Matchmaker have allowed entrepreneurs to capitalize on a destigmatized practice. Entrepreneurs in this sector typically fall into the categories of pickup artists, date coaches and matchmakers, though some may be a combination of a few. In the past few years, the focus has been on cultivating online dating profiles complete with a professional photo and painstakingly crafted biography. A combination of the three categories, Rachel Russo, founder of a New York-based dating and relationship business, offers services including $250 mock dates, where she goes out with a client and delivers a report card at the end of dinner. Her $5,000 combination package includes ghostwriting initial emails on an online dating site, offering weekly feedback on the dates and acting as a wing woman. First Generation FashionRachel Russo, founder of a dating and relationship business in New York. Her clients are mostly men from their early 30s to 50s, and she said they’re not “socially awkward” introverts but typically people looking for more than just a first date, and, of course, willing to divulge details of their love lives. For Marilyn Dollar, going to Bela Gandhi, founder of the Smart Dating Academy in Chicago, made sense as she tried to navigate dating after a more than 20-year relationship ended. “She’s kind of like the Pied Piper of the dating world,” Dollar said. “You want to follow her.” Part of Gandhi’s process can involve having clients send emails to friends, bosses and ex-lovers asking for feedback on why they haven’t found the right partner. Gandhi says her company uses the responses—the client chooses who to email—to enact a dating plan. After setting up an online profile complete with new photos, they check in with clients, typically professional singles from their mid 20s to mid 70s, on about a weekly basis. “We’re in your dating canoe with you, so we want to make sure your canoe doesn’t flip over or hit an iceberg,” Gandhi said. Success here can be measured in commitment: Gandhi said she averages two committed relationship or engagements a month. But getting there can cost clients $5,000 for three month one-on-one packages. Russo also offers a $250 breakup package featuring an Italian meal and a “breakover bible,” a personalized guide to moving on. There isn’t a clear path to the profession. Some coaches start informally with friends or draw on their own relationship experience, while others, like Russo, have related degrees. The dating services industry, which includes online dating sites and matchmakers, contained 3,851 businesses from 2009 to 2014, according to research company IBISWorld. The segment brought in a profit of $293.8 million and is expected to grow another 4.2% in the next five years. But it can be hard for entrepreneurs to put a price on love. “If I give someone the capacity to save themselves from five years of [bad] relationships and only two hours of my time, what is that actually worth to someone?,” asked Steve Dean, founder of Dateworking in New York. Dean, who classifies his work as “relationship management,” was able to work through pricing by increasing his rate until finding one that paid his expenses. He charges $200 for the first individual two-hour session and $250 an hour for corporate clients and uses the money to support himself while working without a salary as the founder of a job recruiting site. Caitlin Huston