Seeing the other topic on where to connect got me thinking and I thought i'd start this one. Have you ever had to change planes in a city where you have loved ones (close family, friends, significant others, exes, etc)? For example, I currently live in Houston but I have family in Dallas/Ft Worth and Charlotte as well as good friends in Atlanta and Washington DC.
For me, connecting in a city where I have good friends isn't too awkward but whenever I have had to connect in CLT or DFW it seemed fairly awkard knowing that close family was near me. I did happen to be traveling through DFW a couple of years ago when we were hit by the grounding of the MD-80s and I had a 12 hour layover there, in which case I rented a car and visited my Aunt for awhile. When I went through CLT a couple of years ago though, my connection was too tight that I wasn't able to go and visit anyone.
If you have the opportunity, do you try and do a long layover so that you can visit a friend or family member?; specially since it's not like the old days where they could go through security and hang out with you in the airport.