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- Yes, And He's A Boat Captain. Meet Chris: Chicago's Most Adventurous Comic.
Yes, And He's A Boat Captain. Meet Chris: Chicago's Most Adventurous Comic.
Chris is adventurous, romantic, spontaneous, thoughtful, and downright adorable. He is a modern day pirate - the friendly and charming Great Lakes variety you can bring home to mom.
Eligible In
January 06, 2026
Nominated by our recent guest Kate (fellow improv extraordinaire), Chris embodies the "yes, and" philosophy both on stage and in life. How else do you explain becoming a boat captain when that wasn't exactly the plan? Life threw him a meandering waterway, and Chris just... sailed with it. Sea what we did there?
But seriously, Chris is fine with a few boat puns on your date—just maybe not the whole time, okay? He's got depths beyond the nautical references. Okay, we're done now. Probably.
What makes Chris special is this rare combination: he's genuinely romantic (without any of the ick factor), naturally hilarious, and proudly nerdy. Think Westley from The Princess Bride meets Ben Wyatt from Parks and Rec. He's the guy who can say romantic things to you in Elvish (probably) while taking you on a moonlit boat ride, which is honestly the kind of energy we all deserve.
His improv background means Chris is comfortable with life's improvisational nature—he doesn't need everything mapped out perfectly. Whether it's steering a boat through Chicago's waterways or navigating the unpredictable currents of connection, he's ready to embrace whatever comes next with humor and heart.
Do you know a woman in Chicago who appreciates a man who's both captain and comedian?
Is she excited by spontaneity?
Is she looking for someone who balances romance, humor, and nerdy passions?
Would she be down for dates that might involve Middle Earth references and actual earth (or water) adventures?
If you know her, let's connect her with Chris. All aboard? Details below 👇
If you or someone you know would like to get in touch, reply to this email or head to EligibleIn.com.
*Please include your full name, some information about yourself, and anything that could help our team better vet you. The more complete the request, the better (i.e full name and photo or social media handle).
**Our guests are single at the time of the interview, but we cannot always guarantee they will be available at the time of your request. We will forward all complete requests, but cannot under any circumstances guarantee an introduction to our guests.
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