H/t to Chris for the inspiration for this thread. 
25. Picard's female officers think the captain's "log" is some kind of wimpy electronic journal.
24. Picard's jumpsuits from Oshkosh b'Gosh
23. Kirk was a strong enough leader to keep Scotty in Weight Watchers until after the TV series. Could have done the same for Riker.
22. Sure, in their respective eras, they were both Presidents of the Hair Club for Men. But Kirk was also a client.
21. Kirk's name is hated throughout the galaxy. Picard is even more beloved in France than Jerry Lewis.
20. There was no Klingon word for "defeat" - until they met Kirk. Conversely, the very syllables "pi-card", although difficult for Klingons to pronounce, form the Klingon term for "wuss".
19. Quick query: what would Kirk have done if the chief of security showed up wearing a ponytail, or if the first officer ordered him off the bridge for his own safety.
18. One question: what would Kirk have done if he saw a female doctor bending over the operating table?
17. How they react to cute, cuddly creatures on the bridge.
Picard: encourage science officer to adopt one.
Kirk: beam their cute, cuddly asses aboard Klingon ship.
16. How they would react to Deanna's mother?
Picard: embarrassed tolerance.
Kirk: bribe Q to time-travel her butt to the Ceti-Alpha system, and let her read Kahn's mind for a while.
15. How they spend their captain's salary.
Picard: wise inter-galactic investments, and an occasional splurge on an ancient archeological artifact.
Kirk: blow it all on purple booze and green-skinned hookers.
14. Idea of a good time.
Picard: Wine-tasting with ambassadors.
Kirk: Toga party with Scotty.
13. Favorite character in 20th century Earth history.
Picard: Neville Chamberlain
Kirk: Wilt Chamberlain
12. What they do when confronted with a living entity that doesn't speak English.
Picard: Try all reasonable and prudent means to communicate
Kirk: If it moves, it's toast.
11. What they do when Starfleet calls with unwanted directions.
Picard: Serious kissing of withered old admiral-butt.
Kirk: Leave communicator off the hook.
10. How would they relate to Counselor Troi's mind-reading?
Picard: Purify thoughts with advanced Zen technique.
Kirk: Might as well get naked. She knows what's coming.
9. How do they use the holodeck?
Picard: Wimpy 1930's detective fantasies.
Kirk: Two words: virtual nookie.
8. Adolescent Years
Picard: Squishing grapes in quaint French vineyard.
Kirk: Dating four-breasted cheerleaders in Xabulon system.
7. Fatherhood
Picard: No known children.
Kirk: All known children.
6. How did they do at Starfleet academy?
Picard: flunked entrance exam.
Kirk: re-programmed Kobiashi Moru. Doesn't believe in defeat
5. What is the result of encounters with unidentified Romulans?
Kirk: fires at them.
Picard: gets fired at.
4. How deal with primitive new civilizations.
Picard: Assist development within parameters of prime directive.
Kirk: Sleep with women, exploit men for cheap labor.
3. How they would react to Wesley.
Picard: Encourage development of mental and leadership skills.
Kirk: Use kid to get to mom.
2. One question. Even though Kirk would turn out to be Wesley's father, how long would he let him stay on the bridge?
1. One Spanish word: cojones
