Order an easy to cut piece of chicken cutlet, if out for fleishigs, or a piece of fish if dairy. DO NOT ever on a first date order falafel in a pita, or spaghetti. BBQ ribs are a no-no, too.
Probably a good idea not to wear heels in such a case as same height.
I would always consider if someone was not for me, whether or not that personw ould be good for someone else I know. My nephew married his lovely wife because his best friend went out with her first and realized that my nephew was more shayach for her than himself. he was right.