Scott Baio + Something's Gotta Give
I watched the 2003 Movie Something's Gotta Give and it reminded me of this show. Towards the end, Jack visits all of his exes and finds out what was wrong with him - sort of like what the life coach did for Scott. At least Scott was not 63 before he found true love - LOL.
Just my two cents.
I am hip to your jive - 'cause I'm the GCL