What It's Like To Go On Bad First Dates For A Living

Bad first dates suck. Imagine if you could hire someone to go on them for you.

Every day I get the pleasure of meeting with incredible singles who tell me all about their horror stories, their online dating mishaps, and, inevitably, “that time that the person I was meeting looked nothing like their photos.” We as matchmakers like to joke that we go on bad first dates for other people all day long. It’s not as bad as it seems, though. In fact, it’s a ton of fun and a really amazing lens to have on people and relationships — there’s a lid for every pot, as I like to say.

Sure, sometimes the “dates” we go on really are that bad. I once met a guy who seemed totally great until I asked about pets, as my client has a dog. He went on an unstoppable rant about how disgusting animals and pets were. Our “date,” which was really just our matchmaking meeting, ended abruptly after that. On these rare occasions, I’m just really glad it was my time and not my client’s. I can look at it objectively, but my client would, perhaps rightfully so, take it personally. But 99% of the time, I feel good about the people I’m meeting. Even if this person isn’t a fit for the client I had in mind, perhaps they’re a really compatible match for someone else. Someone who obviously doesn't like pets. The best way is to go in with an open mind and try to take good people at face value. When I find the good in people, instead of looking for all the reasons they’re a bad fit for someone, the opportunities are ample.

A lot of times these “bad” dates that we as matchmakers go on are really positive, productive conversations with amazing people, who off-paper would never make sense for our client. Here’s the trick: we’re looking for the intangibles — the things that you won’t find on an online profile.

How many times have you gone on a first date, and a second, and a third, only to find that had you been able to ask some deeper questions that you avoid asking that early on (What’s your stance on politics? Religion? Would you raise your kids a different religion? Are you open to relocating?), you never would have bothered? That’s the problem that we solve. TDR matchmakers get to ask those questions up front and in person, and only set up people who are compatible in the intangible ways — something that online dating apps and sites just cannot do.

Perhaps my favorite part of being a matchmaker is having the opportunity to learn about and connect with so many interesting, diverse people who all have stories when I ask the right questions. So, while I may be going on bad dates for other people and sending my clients on dates with the most compatible people I meet, I take every “date” I go on as an opportunity to learn — and hopefully match someone else down the line!