。
I had a date with Jane last night.
Literal
Last-night Jane [with-と] date-[did-した].
デートする ('to go on a date') — katakana loanword from English 'date' turned into a suru-verb. This is the standard Japanese term for the concept; no native equivalent exists. Young-people speech might use 会う ('to meet') to be coy, but デート is explicit. と marks 'with [Jane]' — accompanying person.