をデートに

ask someone out

→ を
phrase Rare #29,398
ask someone out Usually followed by 誘う (さそう), meaning to invite someone on a date. The person before を is the person being asked out.
JA: 彼は私をデートに誘ってくれた。
EN: He asked me out.

をデートに誘ってる

Are you asking me out on a date?

トムにはメアリーをデートに誘う勇気がなかった

Tom didn’t have the courage to ask Mary out.

彼女をデートに誘いたいんだが、とてもその勇気がない

I want to ask her out, but I just don't have the courage.