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"I recently ran into my ex-girlfriend and she looks great and was definitely flirting with me. I keep thinking about her and I want to see if we can date again. There's one hitch—she now has a two-year-old (not mine). I'm not sure how I feel about getting involved with a single mom. Should I go for it?"

Thank you for writing. I'm glad that you are taking some time to think before jumping back into a relationship with this woman—it's always smart to think before acting on an attraction.

First, consider the reasons you ended the relationship in the first place. Have those issues been resolved? Do you believe that a second go-around will be more successful? If you think things could work this time, then start to consider how you feel about her having a child. There's absolutely nothing wrong with dating a single mom, but before you get involved with her again, ask her what she expects out of a man that she dates and decide if you can fulfill her expectations.

Some single women just want to date and have no expectations of a man becoming a father or taking on any parental responsibilities. However, if you are involved in her life, you will most likely be involved in the child's life, and at the very least that means you will need to be a positive role model. It may also mean that you can't stay out all night with her, you may not be able to sleep over at her house, and that her kid will always take priority over your relationship. It may also be that this woman does want a co-parent—if not now then in the future—so be honest and realistic with her about what you can offer her.

I'm glad that you recognize that this is a complicated situation and you are thinking it through. Start slowly, maybe a cup of coffee to re-connect and just make sure you have similar expectations.

Good luck,
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