As Alan continues spending time with his transgendered love interest Paula, he meets her ex-wife Rachel and witnesses their amicable friendship. Paula offers Alan's help with Rachel's back problems, but when he goes to Rachel's house to work on her ailing back, she hits on him. After Paula clarifies that she and Alan are not exclusively dating, Alan goes on a date with Rachel and is shocked to see Paula at the same wine bar. It turns out Rachel knew Paula would be there and arranged the date to get back at her for ruining their marriage by getting a sex change. As they are arguing, Alan realizes the two women still care for each other. Paula and Rachel end up getting back together. Meanwhile, Jenny is baffled when her one-night-stand, Brooke, blows her off. After Walden tracks Brooke down, he learns that she fears commitment much like Jenny does. He convinces her to go on a second date with Jenny, but before the date, Jenny drinks too much alcohol in an attempt to calm her nerves. While Walden tries to help remedy her loopy behavior, Brooke arrives at the house drunk as she too was anxious about the date. The two celebrate Christmas Eve by falling into a drunken heap.