/me rolls eyes at Ustwo
/me is going to ignore the sure to be comments about why he can't have both women...
If he doesn't give it a go wiht Mary - -and ends up married to Jen, would he always wonder what might have been, and would he be truly happy for the rest of his life with Jen? Would he always wonder.
Sounds like he's staying with Jen for now out of duty and obligation, and not wanting to hurt someone... Not because he loves her from the bottom of his toes and she makes him a better person. If he doesnt have the 'toes' and he's only staying out of obligation - that's the wrong reason to stay with somoene. He may love her, as a person, because she's there and comfortable, but is he really In love with her -- from his gut?
Mary is someone new... that may not be the real deal either - or it might... I have no answers...