Movie I saw several times on HBO or Showtime circa 2000; ran repeatedly for about a month, then disappeared forever.  Main character was named Arnie or Artie – his father had died/disappeared when Arnie was very young, so Arnie had been raised exclusively by his mother and sisters.  As a result Arnie became inordinately attuned to women.

FF to Arnie as a very soft-spoken adult, managing an apartment complex owned by one of his sisters.  As a result of his upbringing, Arnie is a near-involuntary makeout artist – the apartment complex tenancy was almost 100% female, and they’d break things just so Arnie would come to fix them – and when the women would throw themselves at him, Arnie didn’t know how to say No.  When Arnie falls in love and gets engaged, though, his inability to turn women down gets him in hot water; his fiancée (a masseuse) leaves him, telling him to learn how to be a “real man”.  Arnie misunderstands and thinks she left because he’s not macho enough.  Very shortly after, meets a guy – a big red-haired pirate-looking guy who’s actually an accountant named Dennis – and Arnie asks Dennis to teach him how to be a real man.  Lessons in cigar smoking, belching and guy fart etiquette soon ensue.

This one’s been hounding me for over a decade.