Misread Moments: How Two Perfect Matches Almost Missed Their Shot

Jorrie Van Sky • August 16, 2023

In the intricate dance of modern dating, even the most promising pair can find themselves tripping over misunderstood cues and unspoken emotions. Dive into a captivating tale of how a professional matchmaker, with keen observation and a bit of intervention, helped steer a seemingly perfect match from the brink of missed opportunity. As you unravel the narrative of Allison and Glen, discover the nuances of perception, the weight of unspoken assumptions, and the true magic of matchmaking that goes beyond just setting up a date. This story serves as a timely reminder that even in an era where communication is at our fingertips, truly understanding one another can still be our biggest challenge.

professional dating service


I've been a professional Matchmaker for over sixteen years and it never ceases to amaze me how otherwise very savvy individuals can stand in their own way when it comes to their dating lives. I've seen this happen over and over again, regardless of the age group or demographics of both people. As a Matchmaker, it's our job to step in and assist when we see this occurring but for all of you out there in the wild doing it on your own... you need to consider the story I'm about to tell you. This past week, I set up one of my favorite clients, Allison, with a gentleman named Glen. Allison is a total catch. She's educated, in her mid- 40's and absolutely gorgeous. When Allison walks in a room everybody turns their head. She's stylish, sure of herself but yet totally approachable. Everyone loves being around her. 


By the way I've described her, I'm sure you're wondering why she's single. This isn't an uncommon scenario- as a busy Attorney, Allison travels alot for her work and has a very full life with friends, family, etc. She has everything she wants except for a long term, committed relationship and she wants to find that... but she doesn't have time to go out on dates unless it's really someone that makes sense for her. Allison is someone I would consider to be on a very selective search for the right partner. Enter Glen... a forty eight year old single Neurologist that just so happens to be as cute as a button. He checked all of her boxes; hit the height parameter, had a full head of hair and smelled fantastic. Glen had been divorced for five years and was at a place in life where he had done a lot of work on himself and was able to make space in his life for a serious relationship. Right when I met Glen I knew I had to introduce him to Allison. 

A few days before they were scheduled to meet, I spent an hour reading all sorts of different restaurant reviews, looking at menus (Allison's a vegetarian) and I finally decided on the perfect place with the perfect date-night ambiance. I confirmed the location with both of them, made the reservation, and waited (impatiently) in anticipation of their meeting. Expecting this to be Executive Connections next success story, I had already arranged a call with both of them separately the day following their meeting to hear how it went. As a professional Matchmaker, this is the stuff that really gets our juices flowing... we get to hear how we did! We get validation for our work, our instinct and everything else that goes into matchmaking busy, single, professionals.


This is where the story can be a learning experience for everyone. I spoke to Allison the morning after her date and she was really confused and disappointed. Apparently, Glen didn't ask for her phone number and or ask to see Allison again when he walked her to her car after dinner. Now, when you work with a professional dating service you need to go into it with the exception that matchmaking isn't a science. There's no magic formula that we use when we're matching two people and that concept is something that, by this point in my career, I understand, at least intellectually. That being said, sometimes you just know you're right about two people and this was one of those times for me. Allison had really enjoyed herself on the date and felt like it had gone pretty well; they were at the restaurant for two hours and she felt like there was flirting on both sides. She was baffled when he walked her out to her car and then said "It was really lovely to meet you, take care". She had been planning on giving him her number and seeing him again. During the date Glen had mentioned how terrible the traffic had been on his way to the date so Allison thought that, coupled with the 30 mile distance between the two of them, had turned him off. Right after I hung up with Allison I called Glen to get the scoop on what happened. Glen's perspective of the date was entirely different than what I had just heard from Allison. 

Glen had really liked Allison; he thought she was beautiful, funny, intelligent- just an overall great person. He thought they were really hitting it off until she shared with her that he was planning on stepping down as the Chief of his department at the hospital to allow more time to pursue his passions in life. He was tired of the administrative tasks that came along with it and it didn't offer any benefit to his pocketbook by holding the position. Glen felt like Allison's energy completely shifted when he shared his plan with her. Maybe to Allison, Glen thought, that made him come across as unmotivated and lacking in drive. He didn't want to make it awkward for Allison at the end of the date by asking for her phone number.

Of course when I heard this I explained to Glen that Allison made no mention of this to me when we were debriefing about their date. Glen had misread the situation and misread Allison's body language. Which is not an uncommon thing to do on a first... second... or even third date. The funny thing is.. Allson liked Glen. And Glen liked Allison. If we hadn't stepped in, there would've never been the happy couple that exists today. 

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