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- unlike "puppy love", 初恋 is not belittling or derogatory, so I'd simply go with first love
- をとっくに済ませた finished, ended long ago. "put an end to" is too active and aggressive.
- 人と -> "with people who...", "with someone who...". The structure of the sentence is 俺は ... 人と ... 付き合うのが好き
"Well, you know, I like women/men whose first love ended long ago, so we can date without deeper feelings involved / without being all lovey-dovey / without falling head-over-heels for each other"
良く言うよ is sarcasm; 2. doesn't agree with 1. and maybe thinks that 1. will change his opinion if he falls in love: "Easier said than done", "Yeah, right", "It's not that easy, man"
If 2. agreed with 1., they'd say something along the lines of "そうだね", "それがいい", or "私もそう思う".
Last edited by noutenki; March 21, 2012 at 09:40 PM.