Episode 12 of "Men in Trees"
s01e12 The Darkest Day

Now that Jack has admitted to Marin hes falling in love with her, she decides to bide her time and wait for his ex-girlfriend, Lynn (Justine Bateman), to leave Elmo. Meanwhile Annie thinks Patrick wont be ready for a relationship until he unties himself from his mothers apron strings, Celia gets a visit from her out-of-town boss, Sara comes back to town and is surprised to see Ben and Theresa back together, and Jane wonders if she wants to keep a long-distance relationship with Sam (Ty Olsson), aka Plow Man.