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The 50 First Dates of Remote Job Networking



By Tory Fitzgerald, Operations Leader and Remote Work Seeker

Any opinions expressed within the blog are those of the author and not necessarily held by Workplaceless itself.


15 years ago, the world was introduced to the world’s greatest movie – 50 First Dates. I know every single one of you is shaking your heads, YES! It’s funny, a great love story and involves adorable penguins, that’s a win in my book! It’s a classic! (Okay, maybe not a classic, but it is good!) This is one of my go-to movies when there is NOTHING on Netflix, Hulu or Prime.


But why will this movie stand the test of time? – Because it is relatable. The core of the plot line is Adam Sandler’s character, (Henry) is trying to convince Drew Barrymore’s character, (Lucy) with repetitive short-term memory loss, over and over again to… love him.




Whether you are going on 50 First Dates with a girl who has short term memory loss or networking to find that perfect remote work position, it's all about quickly convincing someone to love you – over and over and over again.


Networking might seem scary, daunting and a lot of work, but it is far more effective than simply applying for a position. I had the pleasure of speaking with Alice Hunsberger from OkCupid and she gave me a super scary statistic. - They received 6,500 applications for their last remote opening. 6,500!!! Once the shock wore off, I remembered that I am competing with everyone in the US for this position, if not the world!


Trying to convince someone to love you through the written word (resume/cover letters) is very difficult but trying to convince someone to love you, who you already have a connection with, is a whole lot easier. If you remember the scene from the movie when Henry makes a video about the first time he and Lucy met, he didn’t just talk about this meeting, he included some of their friends from the restaurant and even name-dropped her dad. This made Lucy instantly more comfortable and started to build that trust and love for Henry.


Like most people, networking isn’t something that comes easy to me. I’m an introvert by nature. So I decided to work with a career coach to help guide me and kick me in the buttwhen I tried to turn into a hermit again. She had me read “The 20-Minute Networking Meeting” by Nathan A. Perez. This put into perspective what I should talk about, how I should take control of the meeting and what questions to ask. It’s like a dating handbook for networking.


Since my original network wasn’t too involved with remote work, I basically had to build a network from scratch. First I reached out to individual’s on LinkedIn who had in their profile tag – ‘Remote Work Advocate’. From there they connected me to other individuals, resources and networking events (like Workplacelesss Networkplaceless events). Each interaction I had, I took the 50 First Dates mindset – I only had a few minutes to convince this individual to love me. Sometimes I was successful, and sometimes not. Rejection is part of dating.


So far I have set up 26 phone/video calls. These meetings range from simple meet and greets, to company information sessions, to actual interviews. Of those 26 dates, I was stood up twice and ghosted by 3 companies I had actual interviews with. But of the 21 other dates, I was given information or offered a connection that would help continue my search.


One of the best advice I was given was to join Slack. Prior to a few months ago, I didn’t know Slack even existed and now I am active in 6 different channels. My favorites being Remotive, Support Drive and Untethered Success. I am able to connect with other remote work hopefuls, companies that are hiring and individuals that are willing to network. There are even channels that supports ‘speed dating’ for networking!


By this point, I am sure you are wondering… ”Well, have you landed a job?!” Nope. Sadly, I have not. I’ve only been on 26 dates so far. This means I still have 24 to go! Wish me luck!

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