[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/ds9_hisway294.jpg]]
[[caption-width-right:350:Give a round of applause to Vic Fontaine, everybody!]]
Bashir, Odo, Kira, Worf and Dax are in a holosuite watching a jazz performance by the character Vic Fontaine. After the performance, Bashir urges the others to meet Fontaine, who understands that he's a hologram. A self-described observer of human nature, the crooner quickly identifies the love lives of O'Brien, Worf and Dax before the group leaves. Bashir relates how Fontaine helped him woo his current girlfriend, which intrigues Odo.

Kira is leaving for Bajor to meet with Shakaar, her old flame. Quark criticizes Odo for not making a move on her in the year since she's been single. Odo decides to meet with Fontaine for advice. The holographic singer accurately assesses Odo's dilemma and decides that the changeling needs to loosen up. He recruits Odo to pretend to play piano during his next performance. After some befuddlement, Odo gets the hang of it and is suddenly tickling the ivories like a bona fide jazz man. Even while conducting his duties afterwards, Odo is infused with swing.

When Odo returns for another dose of jazz, he's shocked to discover that Fontaine has created a new performer named Lola Crystal, who looks just like Kira. After a dazzling jazz number, Fontaine suggests Odo spend some quality time with Crystal, but Odo can't go through with it because Crystal's personality is too unlike Kira. Kira herself returns to the station, and Fontaine decides to take matters into his own hands. He transfers himself into the holosuite where she goes to meditate and invites her to a date on Odo's behalf. Then he contacts Odo and claims that he's perfected a new Kira hologram for him to practice dating.

Odo and Kira share a date in Fontaine's holographic lounge. The constable is finally at ease and impresses Kira with his relaxed confidence. After sharing a dance, Kira suggests that they take their next date outside of the holosuite, but Odo tells her that isn't possible, which confuses her. Fontaine must ultimately step in and admit that he lied to both of them to make the date happen. Odo storms off, humiliated, and Fontaine shuts himself down.

Kira discusses the previous evening with Dax, who urges her to act on any moment of clarity she has. Emboldened, Kira confronts Odo about last night. Odo finally asks her about Shakaar, and Kira insists that they remain just friends. Kira demands that they talk about their relationship, and the pair begin to sarcastically plan out a date. When Odo mockingly suggests that they skip the date and go right to kissing, Kira agrees, so Odo suddenly grabs her and plants a big one right on her lips. Everyone on the promenade gapes at the couple, but they keep on kissing. Afterward, Odo returns to Fontaine and admits that he'd been right about everything. In return, Fontaine asks only that Odo leave the program running for a few minutes because he feels like singing.

----
!This episode contains examples of:

* ActorAllusion:
** Vic's line "I remember that weekend with Frank" also acts as a little reference to Frank Sinatra Jr., with whom Creator/JamesDarren is a friend of.
** Odo says "bon appetit" and explains to Kira that it's a phrase in an Earth language called French, and then briefly affects a French accent. She asks him if he speaks it, but he denies it, saying he only knows that much. Rene Auberjonois is French by ancestry and both his parents were Francophones, [[https://twitter.com/reneauberjonois/status/329600484765728769?lang=en but he didn't speak it himself.]]
** A negative example when Vic invites Odo onstage and the constable says he's "not a singer." Rene Auberjonois was a Broadway veteran who won a Tony for his role in the musical ''Coco''.
* ActuallyPrettyFunny: Odo makes a small rueful chuckle at Quark pointing out that Odo isn't the most loveable guy in the galaxy, or even in the room (it's just him and Quark).
* AndYouThoughtItWasAGame: Odo is duped into taking the real Kira on a date in the holosuite, mistakenly believing that it's only a hologram of Kira that Vic created.
* AlmostKiss: Odo and Lola, before Odo decides he just can't do it, because he loves Major Kira and she's not her.
* BigDamnKiss: Between Kira and Odo, after over three seasons of leadup.
* BookEnds: Of course the episode begins and ends with Vic singing.
* BreatherEpisode: After three episodes filled with moral ambiguities, this one is about getting Odo and Kira together.
* ComicallyMissingThePoint: Since the context is well-outside Odo's experience.
-->'''Vic:''' Tell me something. How do you get to Carnegie Hall?\\
'''Odo:''' I have no idea.\\
'''Vic:''' Practice, practice, practice. Get it?\\
'''Odo:''' No.
* ContinuityNod:
** Vic was able to create a hologram of Kira due to the events of [[Recap/StarTrekDeepSpaceNineS04E10OurManBashir "Our Man Bashir"]].
-->'''Vic:''' It did take me an hour to get rid of the Russian accent.
** Quark reminds Odo that he had a year to do something about Kira--referencing the Major's breakup with Shakaar just prior to [[Recap/StarTrekDeepSpaceNineS05E22ChildrenOfTime "Children of Time"]].
* {{Fanservice}}: Holographic!Kira in a tight red dress singing "Fever." Very nice.
* {{Foreshadowing}}: Vic's opening song is "You're Nobody 'til Somebody Loves You."
* GrewBeyondTheirProgramming: A minor example: while it's implied that Vic has always known he's a hologram from when he was first activated and observing people and giving them relationship advice is one of his main functions, it's doubtful that he was designed to be able to use the station's comm system to speak to people when he's not activated, move between different holoprograms at his leisure, insert and edit characters originating from other holoprograms into his own, or have the station's computer recognize and execute his commands with his voice input to end his program at his own command.
* JiveTurkey: Vic's usage of Sixties slang goes well over the heads of the 24th Century crew.
-->'''Vic:''' If you're gonna work Vegas in the sixties, you better know the score. Otherwise you're gonna look like a Clyde.\\
'''Kira''': A Clyde?\\
'''Vic:''' A Harvey, you know.\\
'''Worf:''' Har-vee?\\
'''Vic''': A square. ''(getting impatient)'' You ''know'' what a square is, right?\\
'''O'Brien:''' ''(happily)'' It's one side of a cube!\\
'''Vic''': Well, I guess that [[StealthInsult answers my question]].
* LoveEpiphany: Kira's moment(s) of clarity.
* NiceJobBreakingItHero: Subverted. When Odo finds out he's not on a date with a hologram but the ''real'' Kira, they both get pretty upset at Vic for his deceit. Yet it's not long before they get together in the real world anyway.
* NotSoAboveItAll: During a meeting in Sisko's office, Odo begins humming and quietly singing "They Can't Take That Away from Me." Sisko recognizes what he's doing and joins him while going over a report.
* RelationshipUpgrade: ''Three seasons'' of waiting!
* RightInFrontOfMe: Odo's date goes relatively smoothly until he discovers that Vic didn't set him up on a dinner date with a holographic Kira but the actual Kira.
* RuleOfThree: Done subtly and sadly, before the happy ending, as Odo, mortified at finding out Kira is the real deal, increases the distance between them in three steps and three words that, to the attentive listener, convey just how his hopes are fading away:
-->'''Odo:''' Nerys... Kira... Major.
* ShoutOut:
** Music/FrankSinatra, Shecky Greene, and Creator/VictorBorge are all referenced as performers that Vic is familiar with.
** The title, of course, is a play on Sinatra's song "My Way."
* SoProudOfYou: Pretty much the only way to describe Quark's reaction to the kiss.
* TheMatchmaker: Vic Fontaine.