Looks like he's kinda grown attached to me.
* kinda=kind of 在美国口语中十分常用，是“有一点...”的意思
grow attached to 开始喜欢上...
I break off a relationship.
* break off 断交，catch up 言归于好
Looks like those two are up to someithing, huh?
They can come out in the open.
* 那两人最近关系好象有点暧昧，是吗？
他们大可以公开来往。
How am I supposed to ask for a date?
* “约会某人”可以说 ask someone out, ask ... for a date
常用的方式有：
What are you doing this weekend?
Would you like to go out this weekend?
I just don't feel comfortable holding hands in public.
* hold hands 牵手，还有 hand in hand, arm in arm
Well, I struck out this Valentine's Day, too.
* Valentine's Day 情人节
What a drag! I got that "Let's just be good friends" line again.
* drag 令人沮丧的事或物，line 说词
I wonder if there's an easy way to break up and still be friends.
* break up, split up 都是分手的意思
Too bad. I almost thought we had something.
* something 指特别的交情
I see my girlfriend home.
* see...home 送某人回家，see...off 则是送行的意思
He is playing the field.
* play the field 和很多异[屏蔽]往，反义为 go steady
I pretend to give hime the cold shoulder.
* 我故意假装冷落他。
此外 cold turkey 是指冷漠的人
Well, it's over, anyway. Time to find some new.
* 我们的关系完了?梢运 I'm through with her/him. 或
We're through with each other.

很贴近生活！