Winslow was the delegate for eight of the Selected who felt like the Baseball Game was an unfair date that the other Selected had. Chosen by the other eight, he told Eadlyn about their idea for her to come to a group date with the other eight. When he asked Eadlyn to go in the date, he had "puppy dog eyes".
For the date, he was the host who welcomed Eadlyn "to the first ever Selection Variety Show". He joked during the welcoming as well. For his act during the show, he juggled beanbags. Once he got up to six beanbags, he dropped them "with one slapping him on the head". At the end, he danced with the other seven performers.
He is simply descibed as "having a great personality".