It feels like I haven't hung out with him for a while.
It feels like it's been a while since I've gone out with him.
ーIt feels like I haven't hung out with him for a while.
「しばらく彼と遊んでない気がする。」
hang out with ... で「…と遊ぶ」
for a while 「しばらく」
ーIt feels like it's been a while since I've gone out with him.
「彼と出かけてからしばらく経つ気がする。」
It's been a while で「久しぶり・しばらくぶり」
go out with ... 「…と出かける」
ご参考まで！
It feels like I long time since I’ve hung out with him
It seems like ages since I’ve seen him
この文章が以下のように翻訳されています。
彼と遊ぶのが久しぶりに感じます ー It feels like I long time since I’ve hung out with him
彼と ー with him
遊ぶのが ー hung out / played with / seen
久しぶりに ー a long time since I have / ages since I have
感じますー it feels / it seems
参考になれば嬉しいです。
カナダ 
オーストラリア 
