Emotional baggage is a natural side-effect of emotional pain, which everyone experiences in one way or another. A man who has been through a divorce or some other negative life experience is probably going to have some unresolved issues. The important question is not whether he has baggage -- but what he's doing about it.
1. Perpetually Mistreated
Some people have a long history of having been mistreated, taken advantage of or having been abused in past relationships. If the man you're dating has a lot of stories about awful ex-girlfriends and the terrible things they did to him -- two possibilities exist. One is that he has no insight into his own role in the failed relationships and he will probably make the same mistakes with you. The other is that he is exclusively attracted to manipulators or people who will treat him badly, which raises questions about how he perceives you. Either can be a problem, but watch out for signs of misogyny. If he thinks all women are manipulative or crazy, he probably doesn't consider you an exception.
2. Carrying a Torch
It's not uncommon these days for people to remain friends with their exes, so just because the man you're dating is close to an ex doesn't necessarily mean he's still in love with her. However, a man who is still pining over a lost love is never going to be emotionally available to you. The relationship will never develop any real intimacy because his emotions are focused on someone else. This type of baggage is even more of a problem when combined with bitterness and resentment. If he's still in love with an ex but he thinks she's crazy and that she treated him terribly, you can expect to hear a lot more about this woman than you really want to.
3. The Knight In Shining Armor
Some men like to think of themselves as knights in shining armor who ride off to rescue damsels in distress. If you've been going through a hard time -- for whatever reason -- it might feel nice to date a would-be rescuer. Unfortunately, a man who sees himself in this role may lose interest in you, once you're back in a good place in your life. People who seem to need rescuing can be unstable in other ways, so the man who repeatedly tries to rescue women can also be the man whose ex-girlfriends are all supposed to be crazy. In that case, you could end up dating a chivalric misogynist, a man who is perpetually bitter toward the same women he's always trying to save.
4. Insight Makes the Difference
Trying to find a man with no baggage would be like trying to find a man with no life history. It just isn't realistic. However, there's a big difference between people who know about their baggage and people who don't. If the man you're dating has had a lot of bad experiences, listen to what he has to say about them. If he knows how he contributed to those situations and what he wants to do differently this time, then his bad feelings about his past relationships can probably be managed. Insight makes a big difference, with all the varieties of baggage you can run into. If he knows himself well enough, he can work on getting over his issues or at least not being ruled by them. If he has no idea, then he will repeat the same patterns.
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