A bachelor pad overlooking Wrigley Field is home to the close-knit but usually bickering Kolchuk brothers.
Harry drafts a blueprint for wooing an attractive co-worker, while recently separated eldest brother Mike moves in with Harry and youngest brother Billy, a get-rich-quick schemer.
Harry plans an accidental meeting between Mike and his old high-school sweetheart. ""Take-charge"" Mike learns that his estranged wife, Lisa, has been seeing another man, so he decides to a wade into the dating pool with Kristen, the woman he courted before he met his wife.
Normally close-mouthed Mike opens up to Lindsay about a private matter, which makes Harry feel like he's been ""left out in a lonely rowboat---like Fredo Corleone.""
Unhappily married Mike causes trouble before a friend's wedding. Harry confronts Lindsay about having a romantic relationship with him.
The brothers rethink their strategy concerning ""that mysterious creature called woman,"" with old-fashioned Mike trying some newfangled approaches to romancing his latest steady Amy. Then smooth operator Harry shows remarkable patience in courting a comely surgeon.
NBA star Scottie Pippen (in a recurring role as the guys' landlord) joins the cast in an outing about Mike taking his brothers and Lindsay to the Bahamas. While there, Mike is wooed by Bahama sugar mama Nina; Harry has a go-round with the roulette wheel; can-do Billy goes condo; and ""elitist snob"" Lindsay has a fling with a cabana boy.
The love bug bites Mike, who trysts with his estranged wife, and Harry, who finally has a close encounter with Lindsay.
An embarrassing private videotape threatens to ruin Harry and Lindsay's jobs.
Co-workers Harry and Lindsay try not to mix pleasure with business; and entrepreneur Billy thinks he's on to a real moneymaking scheme.
While Harry and Mike argue about meddling in love struck Billy's private life, their little brother puts his foot down and takes a big step on his own. So, it's up to the older Kuchaks to save their impetuous sibling from the mess he's gotten himself into.
The unthinkable happens: an attractive sculptress prefers to get sad-sack Billy in the sack instead of his hunky brother Mike, which leads to ""a family crisis of Biblical proportions.""
Billy's latest moneymaking scheme ends in disaster.
When her designing mother comes to town to see her receive an architecture award, Lindsay frets that the woman is there to steal the spotlight from her. Meanwhile, Mike and his macho pals engage in a contest to see who can keep from crying during Brian's Song.
