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After widowhood: Matchmaker helps me learn to date again


“What are you wearing this evening?”

If this were a spy movie, I would either be a hero on a top secret mission, or the spy that gets killed in the first ten minutes of that movie whose death has to be investigated by the real hero. My personal mission, which I have chosen to accept even though it sounds nuts, is to find out through a series of questions and body language whether I am about to meet a new friend, a funny anecdote, or perhaps the next love of my life.

I’m on a date. A blind date. Set up by a matchmaker.

Hopefully, this night will not self-destruct like the tape on “Mission Impossible.”

The first chapter of my dating life was rife with Internet weirdness, mixed signals, sad bouts of psycho-dialing (mostly by me).When I got married, my husband and I used to snicker smugly that we would, as the late goddess Carrie Fisher said in “When Harry Met Sally,” never have to be out there again. Yeah, so that was premature.

About a year after unexpectedly losing my husband, I tentatively signed back up for Match.com and eHarmony. My standards were, apparently, too high for the dating pool, because that pool needs draining. Men my age seem to think they should be dating women in their 20s, and the men who think they should be dating me are my mom’s age or older. Sigh.

In the middle of a rant to a friend about just buying 12 cats and being a sad alone widow forever, she sent me a link to a site called Tawkify, a San Francisco-based matchmaking service co-founded by legendarily sassy Elle Magazine advice columnist E. Jean Carroll.

“I know it’s more expensive than the normal online sites,” she wrote, “but you should check it out.”

Tawkify starts with an online query and then leads to a recruiter, who explains the basics. Accepted clients are paired with a matchmaker, who will do a painstaking interview with you, then pair you with other suitable and background-checked clients in your area. The matching process is done by humans instead of computers, which I liked because the computers have not been impressive. You’re killing me, robots!

The biggest difference between Tawkify and online-only sites - besides the price, which was about $1,500 for a three month membership and three dates, or $500 a date - was that I would see no profiles and no pictures. I wouldn’t even know the date’s name until the day of. It sounded crazy and mildly terrifying, but intriguing. I was in.

About a week later, I was introduced by phone to Olivia Balsinger, my new matchmaker. Forget the crone-like scarf-wearing yentas from “Fiddler On The Roof” - the woman I was asking to make me a match, find me a find, catch me a catch, etc. was a peppy, pretty New York-based 20-something. We bonded over being journalists - she’s a travel writer - and her goal to combat what she called “the swiping culture” of Tinder and Match.

Having a matchmaker, she thought, was a perfect place to start for someone like me just getting back into dating and “getting your feet wet, which can be exciting or terrifying. Having a matchmaker is like having someone to hold your hand, like having a friend.” I told her my criteria - men no more than six years younger and ten years older than me, OK with a young child, and employed in a real job that pays in currency and not, I don’t know, pizza or heirloom tomatoes. (I also figured the price was a deadbeat deterrent.)

My very first date was at Lake Worth’s Bamboo Room. All I knew about the guy was that he had never been married, but was funny, in sales, and Jewish, just like my late husband. I had a few friends on deck to “accidentally” show up should things get weird, so I felt OK about it in a low-expectation sort of way.

Olivia asked me to approach the date optimistically but with realistic expectations because this was just the beginning. It’s what the TVLand show “Younger” calls the “Bad Pancake” theory, which holds that the first stab back into romance might be misshappen and messy but was necessary to get out of the way.

“Remember this is a first date,” she texted as I made my way up the wooden steps to the bar. “We want to get you out there and from there, we will shape what does and doesn’t make sense going forward.”

When I got there, Mystery Date was late, and the rest of the club was being set up for a special event. I knew the bartender from my cocktail reporting days, and upon finding out why I was there, he bought me a drink. When the guy finally arrived, I knew three things - he was good-looking, very nice and that we were not going to be a thing. We had a pleasant, if circuitous, conversation, in which I found that we were in different places in our lives.

Also, he openly checked out the butts of two ladies at the bar behind us. So, no.

Still, it was almost a relief to get the first date in the books. And the special event at the bar turned out to be the afterparty for the wedding of a guy I knew from around the local music scene, so after the date I stayed and reconnected with a lot of old friends.

In my follow-up with Olivia, she explained that she thought that First Date and I would have similar senses of humor and things to talk about, and said even though it wasn’t a match, that my feedback would make the second date even better. And it was! Second Date was an engineer from about two hours away, who drove all the way up to Delray Beach on a weeknight to have drinks that turned into dinner and a three-hour conversation. He told me I was beautiful. He said he wanted to see me again, made sure he had my number, and then sent a text to Olivia the next morning confirming I was pretty and smart.

And then he completely ghosted on me.

Oh, well. That was disappointing, but If I’m not your thing, man, Godspeed. Olivia said that the guy found the more than two-hour drive between us, as well as our busy schedules, to be an issue. Next!

Enter Third Date, who Olivia thought had a good chance of going somewhere. He was in the media, in a different city, was smart, and of an appropriate age. My mom had given me a gift certificate for a night away, so I offered to meet up at a restaurant in a trendy area near him, so even if the date went badly, I still had paid-for room service on the beach without a toddler. That alone is worth the drive, amiright, moms?

Surprise! Third Date and I hit it off immediately. We dished about hipsters, food and dating in your 40s. I wasn’t sure if there was a romantic spark, but we talked for hours, split some appetizers and walked around chatting for three hours. By the evening’s end, I was confident that this was not the next love of my life, but that I’d at least made a real friend, and not just a “Let’s be the kind of friends that never see each other again since we’re not making out” kind of friend.

Since this was to be a learning experience, I followed up with both Olivia and Third Date. He told me that I was “great in conversation and (was) clearly on top of the pop culture world and what informs it, so we had a lot to talk about there, which was entertaining.”

The deal-breaker for him was “that I think I don’t want to be dating in the industry.” He also told me that on our date he felt sometimes like he was an interview subject, something he’d been cautious about doing as well. Good to know. We’re still in touch, and I sincerely wish him good luck in his search. And real good luck, and not “Since you don’t want to date me, I hope you get eaten by the Sharknado” kind of luck.

When I talked to Olivia, she said she had high hopes for me, complimenting my “sunny disposition and how you see the best in everyone,” and thought that would be my biggest asset as I continued dating. “Continue to be open-minded. That’s the hard part for a lot of people. You already have so much love to give.”

Yeah, I do! So what did I get out of Tawkify?

I got to safely stretch my legs, work on my own habits like my nervous over-talking, and remember what dating is supposed to be - sitting across from a new person, getting to know them and getting out of your own head enough to make a connection. Also, maybe some free avocado dip. If it doesn’t work out, at least you had dip.



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