と付き合う

to date; to be in a romantic relationship with, associate with someone; spend time with someone

→ と
phrase Common #4,773
to date; to be in a romantic relationship with Used when someone is romantically involved with another person.
JA: またトムと付き合うつもり?
EN: Are you planning to date Tom again?

またトムと付き合うつもり?

Are you planning to get back together with Tom?

あなたはトムと付き合うのだと思っていました。

I thought you were going to date Tom.

両親は私が男と付き合うことを絶対に許そうとはしなかった。

My parents absolutely refused to let me date a man.

君が彼と付き合うのは認められない。

I can’t accept you dating him.

マットと付き合う

I'll date Matt.

— アバウト・タイム ~愛おしい時間について~ (2013)

いつまであの女と付き合う気だ

How long are you planning to keep dating that woman?

— ファイト・クラブ (1999)

君が彼と付き合うことに賛成できない。

I can't agree to you dating him.

phrase Rare #34,927
associate with someone; spend time with someone Depending on context, this can also mean dating someone.
JA: すぐに諦めるような奴と付き合うのはやめろ。
EN: Stop associating with someone who gives up so easily.

日本人は友人と付き合う時はとても丁寧だ。

Japanese people are very polite when interacting with their friends.

すぐに諦めるような奴と付き合うのはやめろ。

Stop associating with people who give up so easily.

地元人と付き合うのは危険ですよ

Dating a local is dangerous.

— RRR (2022)

彼と付き合うのは難しい。

It’s hard to date him.