Everyone has at least one thing about themselves that they’re not looking to highlight. While you shouldn’t lead with your faults, you should certainly own them. So while you’re working on your bad habits, learn how to broach them and mitigate them with a potential partner. If it doesn’t come up in the initial conversation (“I smoke but I’m working on quitting.”), it can be a difficult conversation to start. Try a gentle approach, “I know that you’re a libertarian and I’m a communist so I was wondering if we could have a conversation about that.” At the end of the day, it’s more important to get the potential deal-breakers on the table sooner rather than later – just not on the first few dates.
Now, while women feel some odd compulsion to divulge all our secrets upon meeting, men are not so forthcoming. So when a man admits something not-so-flattering about himself, listen to him. Do not empathize with his story by offering stories of your own. He’s not looking for validation through knowing that everyone has flaws. He might be telling you something very important so pay attention to words, body language and general attitude. For example, if he’s confessing that he’s been known to cheat on his girlfriends and he seems a bit matter-of-fact about it, he may be looking for tacit acceptance of that fact and/or eventuality.
Typically men don’t speak as much as women do – reduce what you say and pay attention to what he says to balance that out.