I am a 26 single female. I have been dating since the age of 19 and unfortunatly havent found my beshert yet. I recently found out that my boss ( age 45 and father of 4) is getting divorced and is intrested in seeing " if things could work out between us" when his divorce finalises. He's a nice guy and i guess i could give it a chance, but i'm not sure what everyone else would think - Is there a problem there? ( his oldest daughter is 20). I also see him through my eyes as a married man.

Halachically the recommendation is that a person should marry someone close to his own age. I think if you read your own letter carefully you'll see that you don't feel comfortable with the idea.