Gabby embarks on her 50 Dates, 50 States series in Connecticut by going on two blind dates on the golf course with the help of coaches Uncle G and Evan. James and Matt compete in a scramble match where the loser faces a brutal armpit waxing penalty. Ultimately, James takes the victory, leaving Matt to suffer the waxing punishment.
Result: James wins the blind date challenge, and Matt's side loses, resulting in an armpit waxing punishment.
Stakes: The losing coach and player have to get their armpits waxed on camera.
Gabby meets her two blind dates, James and Matt, and the coaches assign their players.
James sinks a great putt and celebrates with Uncle G and Gabby.
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