Dean has a small role as a nervous schmuck who doesn't know how to deal with girls. Hey, Martin Milner was an attractive man who was surely no slouch with the ladies, and I can buy Dean as jittery, but I don't know if I buy him as a lovelorn loser asking Marty for tips.
It's a reasonably amusing episode with a dose of typical sitcom misunderstanding. I wish Dean had a bigger role so he could be more directly in the hijinks.
Here's a shot of a young Sheila James, who causes her share of trouble in the story:
Overall, it's an interesting watch for fans of early TV, and I loved seeing it on the disc, but it's not essential Dean, and it doesn't offer quite as much angst as his anthology appearances of the era.