I just LOVE dinner dates!
Some things to consider~~
Best scenario is when it's an outcall and the hotel has a great restaurant. This way I can go to the client's room to leave my bag (candles, ipad with music, condoms, lingerie, massage oil) and we can go down to dinner together.
(you know, like a REAL COUPLE

)
No separate cars getting to a restaurant/separate cars riding back to the hotel or my incall.
No other transportation issues like he comes to my incall to pick me up and then we ride together to a restaurant and back. Or me going to his hotel and then we ride in my car together or take a taxi. All just not ideal scenarios.
Then meeting someone new is always weird in public. "Are you Bob?" "Are you Rose?" ... or we're making tentative eye contact and just not sure if the other one is the one we're meeting.
Can't beat someone giving me his room number and me knocking on the door LOL! So we know whom we're with right from the start.