Missed Connections

It all started with a cold.

If she hadn’t been feeling sick, Kelly wouldn’t have been in dire need of a bowl of matzo ball soup. And if she hadn’t gone to Milwaukee’s famous Benji’s Deli to get it, she never would’ve noticed the tattooed stranger sitting at the other end of the counter.

Though she wasn’t feeling well enough to flirt, Kelly couldn’t get her mind off of Isaac. And later that evening, she found herself typing out a Missed Connections post on Craigslist. As fate would have it, Isaac went back to Benji’s that same week and was informed by a friendly waitress that someone had written about him.

A quick email led to a blind date, which promptly led to a second date exploring everything Milwaukee has to offer. Ten years later they’re married with children.

Here’s their story.

How did you meet?

Kelly: In March of 2013 I was at work and not feeling well. I had a lot of plans that weekend and was like I’ve got to get better. I wanted to find some matzo ball soup, which in Milwaukee is really hard to find. I went to Benji's Deli in Shorewood and sat down at the counter, had my soup, had my breakfast and all that, and looked across the counter and saw this guy. 

I was sick. I wasn't there to flirt or anything else like that. And I just kind of watch this guy from across the counter and I kind of noticed his vibe, his attitude, all of that. And I was like, Man, there's something about this guy. But I was like Forget it. Milwaukee’s small enough. I’ll find this person some other time somehow, some way. And so I left and finished up my day at work, I got home and I'm still thinking about this guy. 

Isaac: There was no chance that you would ever run into me again, because I didn’t live in Milwaukee. I was traveling to town to for my job. And I had traveled to town enough times that I had a couple of regular restaurants that I would go to as soon as I would land. One of them was Benji's Deli. 

This particular morning. I remember I was having my breakfast and it was pretty much empty. And a woman came in and sat diagonal from me. I definitely picked up on her, but she would not make eye contact with me. And that kind of left me feeling like Well, I guess it’s time for another great day. I assumed that I had offended her somehow. And then I just left and went about my day.

Kelly: I sat down at my kitchen table that night, because I was still thinking about it. I was like, What am I going to do? I guess I'll just like throw it out to the universe and I'll write a Craigslist missed connections ad. 

Did you expect to get a reply to your post?

Kelly: I was kind of just compelled because I was thinking about him so much. It was like, I knew there was something there. And instead of leaving this to see if one of my friends can help me I’m just gonna throw this out there and put it out in the universe and see what happens. Why not? 

Isaac: Let's fast forward a week. I've been in town for work for a full seven days, and I decided to go back to Benji's Deli. I sit down at the counter and the waitress looks at me and immediately kind of gasps and says “Did you see your missed connection?” And I admitted to her that I had absolutely no idea what she was talking about. And so she pulls up Craigslist on her phone and shows me this very, very endearing description of me. And I said “Well, what are you gonna do? That was a whole week ago.” She took a step back and looks at me and goes “Dude, you can email her.”

And I think that very night, we started communicating via Craigslist. We decided to go and meet each other on what was basically a blind date.

What did you think when you read the ad? Did you know who had written it?

Isaac: By deduction, I concluded that it must have been that woman that I vaguely remembered from a week ago. I thought it was odd. And I was really, really trying to remember precisely what she looked like. So when I go to this first date, I'm sitting there waiting on her really trying to check every single human that walks in through the door to be like, Okay, is that her? 

What was it like meeting her and actually talking to each other for the first time?

Isaac: We immediately connected. We were both telling rapid-fire stories and comparing life experiences. Dinner went really, really well. And after dinner wrapped up she was like “Let’s go get ice cream.” 

Kelly: Custard. 

Isaac: Custard, right, because we’re in Milwakuee. And so I jump in this strange woman’s car and she drives me off to go get frozen custard somewhere on the other side of town.

Kelly: He had said to me “I’m not from town, but I’d like to go out.” And I was thinking Where could he be from? Chicago? Madison? And when we sit down and I ask him where he’s from he says Connecticut. 

We wound up having a really nice date and we kind of left it at the end with “Next time you’re in town, give me a call.” And at the time I was chronically first dating. You had to really capture my attention at the time to get me to give more of myself to anybody. I actually went on another date the next night with somebody else which went terribly. And Isaac contacted me later that week and said “Hey, my travel got extended, do you want to go out Friday night?”

What did you do for your second date? 

Kelly: This date has a name. We called it The Full Milwaukee, because there were a bunch of things in Milwaukee that I hadn’t ever done before that I wanted to. 

I picked him up from his hotel at six, and we went to a big brewery in town that has a tour. And they have a huge beer hall and we did their fish fry. From there we went to my favorite view of Milwaukee up on top of the hill, and then went out to a cocktail lounge called Bryant’s. From there we went to a place called Koz’s Mini Bowl. And then we went back across town and went to Wolski’s and we closed it. You get a bumper sticker on your way out, it’s a very Milwaukee thing to do. 

And then at 3 a.m. we went and got breakfast at Ma Fisher’s. And by the time I dropped him off at his hotel it was about 5 a.m. and he had to be at work in the morning. 

How did things grow from there?

Kelly: We kind of just never stopped talking after that. He actually came over the next night for leftovers at my house and then took off after that weekend. He wasn’t back again for about a month later. We didn’t date anybody else in between and just kept seeing each other every time we were in town. 

Isaac: We got into a very good rhythm of her coming to see me or me coming out to see her every few weeks.

What’s the secret to a good “Missed Connections” post? 

Kelly: Writing something nice and writing something genuine is part of it, but I also had a qualifier in there of being able to identify himself. I was like “You have a distinct forearm tattoo, if you can tell me what it is then I’ll know that it’s you.” I wanted to make sure I wasn’t getting a creeper and was being a little safe. That’s kind of a woman’s point of view of how to put yourself out in the universe safely. 

In a lot of ways, everybody’s a stranger when they meet. It’s just a matter of whether they met at a bar or Craigslist or on a dating site. One way or another it’s two people who are out there trying to connect with somebody else and find the right connection. 

Isaac, what’s the key to having a good demeanor to attract people?

Isaac: I’m pretty sure she witnessed me casually flirt with the waitress. We had I guess the kind of connection you have when somebody knows what your breakfast order is. I think she witnessed me flash a smile and be polite and friendly with the waitress. I think that’s what it was.

🤔 Poll

📊 Last Week We Asked…

• [poll] “What’s your ideal first date?”

  • 44% said “Casual: Coffee at a cafe”

  • 28% said “Semi-Casual: Drinks”

  • 5% said “Formal: Nice dinner”

  • 23% said “Activity: Hiking, cooking, concert, etc”

And a meet-cuter shared: “I'm older now, so I don't really need anyone to court me. I like to get to know someone on equal standing, exploring common interests, rather than worrying about who will pay the bill or how it will be split at a restaurant.”

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Interviewed and transcribed by Nicolas Vega. This interview has been edited for length and clarity.