"You know how when you break up, you say things you don’t mean? Well, he says the mean things you don’t mean, but he means them."
―Elaine, about Alan

Alan was set up on a date with Elaine Benes by a mutual friend. He was played by Tom Gallop and appears in "The Andrea Doria". Elaine likes Alan, but ends the relationship when she finds out he is a 'bad breaker-upper', feeling breaking up well is one of the most important parts of a relationship.

When Alan ends a relationship, he hones in on something awkward about his ex-girlfriend and makes fun of her about it. Some of his former lovers are so racked with anger over Alan's painful jibes that they physically attack him if they run into him later on. When breaking up with Elaine, Alan calls her 'big-head', and claims her head is too big for her body. Elaine laughs it off at first, but grows very self-conscious about Alan's insult as time passes. To get over it, Elaine meets up with Alan to show him she wasn't affected by his comments, but winds up attacking him when he tells her she not only has a very large head, but also a noticeable bump in her nose.

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