How to Date a Man with Baggage

He's cute, sweet, but complicated. You want to date him, but he's got a lot of baggage. Before you throw away his number, come up with a strategy. There's a way to handle a man who comes with a few twists without losing yourself.

1. Manage outsiders.
Avoid interacting with an "ex-wife" and "baby mama". Technically, a woman that falls in this category is outside of your relationship. As a result, you have no reason to talk to her. If the person approaches you and acts inappropriately, give the job of straightening her out to the man you're dating. Besides the fact that he knows her better than you, he also needs to show her your relationship is important and demands respect.

2. Set clear boundaries.
Whenever you date a man with baggage, you have to set "clear" boundaries. Tell him when you want to have outings involving his children or go to court for any pending case. Be honest about your feelings in order to reduce the number of misunderstandings and awkward situations between you and him. In addition, give him notice as to when you may want to increase your participation in the more "delicate" areas of his life, like when you're in a steady relationship or engaged.

3. Show him compassion.
Put on your angel wings and show the guy you're dating compassion. Understand that everyone makes mistakes (including you) and the last thing he needs from you is a run down of how stupid he was or is. As long as he is making steps to correct his prior errors, he's on the right track. Consequently, you can keep up his spirit by reminding him of this very thing as he struggles to deal with his issues.

4. Let him handle his past.
Avoid falling into a common pattern. While dating a man with baggage, don't try to resolve his current problems that are a direct result of his past. Let him pay off his own debt and find a place to live based on his present salary. Only pitch in funds after you are in a committed relationship, with a ring on your finger and a piece of paper in your hand. If you decide to help out prior to having these three things, you may be sucking on sour grapes and out a lot of money that you can never get back.

5. Know when to let go.
Knowing when to let go of a relationship is key to dating any man. On paper, write down what your "deal breakers". What don't you want to put up with from the opposite sex? If you start to see these qualities in the man you are dating, cut your losses. End the relationship and move on to someone else better suited for you.

These are five ways to approach dating a man with baggage. Use them on your search for Mr. Right. He might just be the guy with a sketchy past who's now ready to change.