I would agree that asking your sister for her opinion first is probably a good idea. She would know her a little better than you, and she would probably know if she was seeing someone that you don't know about. Maybe get your sister to plan a small get together so that you hang around her more than just at work. After a while of that maybe just ask her out as friends, maybe dinner and a movie. With your recent divorce I'm sure she's aware of, just tell her you would like to get out and do things again but just as friends. As far as someone mentioning the age difference 26 & 21 is not that big of a deal, however her age and your two kids might be. I was married at 19 and I was ready by the time I was 21 just hasn't happened yet, (now 23)but some people aren't ready at that age. That might be something to ask your sister about also. How she would feel about dating someone with kids. Hope all works out for ya.