Episode #305 "Tonight's the Night"

It's Lily's birthday, and Sean and Claudia are throwing her a party at The Red Boot Pub. Lily and her friend Alison are putting up decorations, and Lily tells her that tonight may be her "big night" with Dean. It just feels right. Sixteen's the perfect age, and she and Dean are connecting on every level. Dean doesn't know yet; she's going to surprise him. Lily tries to get some condoms from the bar's condom machine, but it's broken, so Lily sends Alison to the drug store. That can be her present to Lily! Alison gets the condoms and later asks Lily why her dad is so buddy-buddy with Dean. Lily admits that it sucks. It was so romantic when they had to sneak around, but now Dean and her dad talk sports all the time and even wash the Finnerty's car together. Alison asks her if she's sure she wants to sleep with her dad's best friend. Lily's walking over to Dean when Brad appears in front of her with a gift-wrapped package and says "Happy Birthday." Lily says it's sweet, but she can't accept the gift. She's with Dean. Lily tries to talk to Dean, but Sean insists on making a toast and revealing to the world that Lily's nickname used to be "Freckle Monster." Claudia, with Henry in tow, tells Sean she's going home; the bar is no place for Henry. Jimmy's had too many of Eddie's hot wings, and now he's sick. Sean tells Claudia they may have to stop at the emergency room. They all leave together with Eddie now in charge. Lily asks Dean if he wants to leave. He hesitates, because he doesn't want to miss the cake, but Lily tells him she has something better. He finally gets it. The Finnertys arrive back home, and Claudia finds Lily upstairs. She automatically assumes that Lily's hiding Dean in her bedroom. Lily admits that she came back to sleep with Dean, but that didn't happen. Dean and Lily are making out, and she tells him how glad she is that she waited. She wants Dean to tell her how he's feeling, but he couldn't be more oblivious. She tries to help him out by asking what about her makes him happy. He strikes out again. Lily decides that maybe this wasn't such a great idea. Claudia tells Lily she's really proud of her. It wasn't easy, but Lily made the right decision. Brad enters, clad only in a towel, looking for his sock. Claudia's horrified and demands that Lily explain how this happened. Lily says she was surprised too. Lily's sitting on the porch alone with her thoughts when she sees that Brad's alone on his porch also. He comes over, and Lily tells him what happened. She just wanted Dean to say some stuff, to feel some stuff. And Brad proceeds to say, quite sincerely, all the things she wanted to hear from Dean. Before long, Lily grabs Brad and kisses him. Claudia tells Brad that for his own safety he needs to sneak out without Sean seeing him. But Sean sees Brad as he's coming down the stairs. He has no idea what happened and advises Brad to stop pining away for Lily-it's never going to happen!