Awesome is at the Buy More looking for Chuck. Instead he finds Morgan. Awesome explains that he wants Chuck to find another place to be, so he can have a romantic evening with his lady. He actually calls her his lady. In that smarmy kind of way. Morgan bravely asks what this entails. Flowers, candles, jumbo shrimp. Ellie's got shrimp issues. Awesome has only been in love with Ellie for like three years, Morgan's dedicated his life to knowing Ellie factoids. He's the expert and gives Awesome some advice on how to make her dream date.
Montgomery is mixing another martini and assessing his raw material. He asks to see Chuck's opening move. Which involves wiggling eyebrows and finger guns. It makes Sarah giggle. Montgomery says being himself won't work. A hot girl like Sarah would never fall for a guy like Chuck. Sarah says she would. Montgomery doesn't believe it. He forces them to kiss to see this passionate side of Chuck. He gives her a peck. Montgomery says he picked the wrong agent. He'll get Casey to do it. Chuck grabs Sarah and gives her a hot, HOT, HOT kiss. Sarah's befuddled and runs off to fix her lipstick. Montgomery winks and says it doesn't seem like their first time doing that. Chuck tries to play it off professionally, and Montgomery promises lessons on bagging Sarah as well. But first, Julie Cooper. Casey listens on via headphones and is horrified.
Chuck is all suited up, and is putting in an earpiece. Chuck tries to break the ice and tells Sarah that they probably have the strangest relationship in all of LA. Sarah cracks that Morgan is still dating, so it's not that strange. Ha. Love when Sarah's funny. She tells him he should be himself, because it worked on her. Then Montgomery walks in saying he needs protection. Chuck adorably says he doesn't think it is going to get that far. Well, not on the first date, Chuck isn't that kind of boy. Montgomery means the other kind of protection. A gun. Apparently, Julie Cooper is known as the Black Widow because she kills all her dates. Is this because they refuse to buy her popcorn at the movies? Sarah looks a smidge nervous.
Lester is called into Big Mike's office. The displays the boss wanted aren't up, and Lester's trying, but they just aren't listening to him. Big Mike says the people need to fear him. Take a lesson from Animal Planet. Go after the wounded gazelle.
At the swanky party, Chuck's inside, Montgomery and Sarah are outside. Montgomery pointedly tells Sarah it will be a miracle if Chuck survives the night. Was there not another agent available for mission: seduce Julie Cooper? Because Chuck's got all that important intel just roaming around in his brain. It wouldn't be so great if he fell victim to the Black Widow. Anyway, Chuck hears Montgomery's comment on the earpiece and Chuck thanks him on his walkie-talkie watch. Montgomery's going to walk Chuck through his four-pronged seduction, which involves making an entrance then getting her liquored up by bringing her an ice-cold dirty martini with three olives. Charles Carmichael orders her beverage of choice, but Julie Cooper is on the wagon. Julie Cooper heads to the bar where Casey is working. Chuck is discouraged because his date lasted 12 seconds, but the good news is he isn't dead yet.