I’ve had the opportunity to observe first hand or here from a girl firsthand how a first date went. One thing that always makes me laugh is guys that spend the entire conversation talking about their life mishaps (not in a funny way but in a complaining depressing way) and about how bad their ex is. I just want to take them aside and shake them. This is not going to win you another date.
Of course, you should be honest about your past. But if anything about any ex come’s up during the conversation, answer it quickly and politely then move on. You don’t need to start that subject early on. If the girl wants to talk about hers that is not your problem. Listen and make a mental note she might not be ready to date.
But when it comes to your ex leave her in the past. And this not only goes for ex’s you don’t like or had terrible break ups with, this goes for the ex who’s still a good friend. Even if you get along great with your past, your future might not be so keen on hearing the juicy details over a cup of coffee or dinner and wine.
Remember a lot of women are insecure. So bringing up the past can do a couple of things that would hurt your chances of a healthy relationship. One it could make them start comparing themselves and seeing if they match up. Two it could make them worry that you are stuck on the past and can’t get over it. And three it could cause them to wonder if you will talk negatively about them should things not work out between you.
So answer questions quickly and shortly and move on. Or say you’d rather not talk about that on a first date.