Awkwardness is to be expected so don't stress on that. Important things to remember: 1) communication is everything. If somehing becomes uncomfortable, say so. 2) Jealously can occur, hence why #1 is so important. If jealously starts to set in, I recommend not going forward with a relationship until each party member has worked out their emotions. 3) If you doo ateemp a threesum, things might not go smoothly the first time but a few more experiance can make all the difference.