what is he trying to say? should I keep going with it ?

Crystal
So I've been talking to this guys on and off for about 6 months now , we're both in High school , so today we were talking about the things we regret and he said he regrets getting with and talking to a lot of girls this year. ....... Am I supposed to be ok with that ? Is he trying to show off and look cool by telling me that ? I don't know what to think about that?