In this two-parter, Frasier hosts a benefit party and finds himself unusually lucky when he manages to make back to back dates with three women. Unfortunately, Sherry torpedoes his chance with the first one with her usual brassy antics. The morning after, Frasier is pleasantly surprised, but confused, when Martin announces he and Sherry have broken up...
In a B-Plot, Roz runs into a former high school classmate after going for a run in a ratty sweatshirt, and tries to figure out how to make sure he (and the other people who lived in her old home town) know she hasn't completely lost her looks.
Tropes:
- Brick Joke: Sherry had earlier commented on Niles' always seeming to be leaving whenever she sees him (not realizing he's making excuses so he doesn't have to spend time with her). In The Stinger (both episodes use the same one), Niles is in Nervosa waiting for a date—and makes an excuse to leave when Sherry shows up a minute after his date does.
- Fake American: In-Universe. A Running Gag of the episode has Daphne trying an American accent, which Frasier critiques as:Who is your tutor, a drag queen?
- Hypocritical Humor: Frasier reassures Roz's worries about her classmate going back home and telling everyone she looks horrible now by asking her if it really matters what people from her past think about her. After she admits he's right, he calls up Norm Peterson to brag about having three dates.
- I Need to Go Iron My Dog: Niles' excuses himself when Sherry shows up with a ridiculous version of his usual "I have to go to a group therapy session" Running Gag.Niles: Last time I was late, the compulsive gamblers were betting the passive-aggressives they couldn't make the over-eaters...cry.
- Moment Killer: Sherry manages to ruin two dates in a row for Frasier without even trying.
- Never My Fault: While Sherry and Martin were definitely a bit of a Moment Killer, the thing that completely ruined the first date was them accidentally exposing the fact he was lying to the woman by claiming to be a dog-loving vegetarian.
- The second time around, Sherry mistakes the second date for the first date and exposes the fact that Frasier hadn't told her about said date. Of course, the real deal breaker was the fact that said first woman broke up the second woman's marriage, something Frasier was unaware of.
- What You Are in the Dark: After talking with Sherry, Frasier realizes that Martin broke up with her because he panicked after they told each other they loved each other. Despite the fact Marty would probably never find out if he did otherwise, and despite the fact doing so will most likely ruin his third date and definitely ensure Sherry will be staying in his life, Frasier still helps them patch up their relationship.
