He shouldn't be saying that to you first of all, even if that is how he truly feels. He definitely wouldn't appreciate it if you started talking about some ex boyfriend you were in love with. That's a big time dating mistake...His words are exactly how he feels, there is no underlying meaning. Guys pretty much say exactly what they mean, very different from women. He's just a little upset that it didn't work out...In what context was it said? Did he sound depressed when he said it? Was it said in an uplifting tone as if he is moving on? What was his body language like, etc.? These are all factors. But, basically I think there is no underlying meaning to it.
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It is possible that he is saying this to get your sympathy and thinks it might be a technique to manipulate your feelings. Makes no sense talking about past relationship to you. After all, you are a potential romantic partner not looking to be a friend to comfort him.
If a girl of romantic interst to me talked about her ex, I would be very upset. So, I can not understand your poinnt of view. May be you like being sympathetic.
If a girl said that to me, I would ask her to come back after sorting out her feelings and when she has moved on from it.
I think it means he really loved that girl. But it is over now. (Emphasis on being over now.)
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That he really loved her, but things are over between them. It's not that hard.
means he still has some feelings for her, but knows it's over now.
Sounds like he misses their relationship.
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