Q: Hi Amy, I recently met this woman I really like, who also happens to be a single parent. I would like to engage a relationship with her but I have never dated a single mother before. I am wondering if you could give me some advice on how to make this relationship work for the both of us? – Vivek from Los Angeles

Amy: Hi Vivek, Entering a relationship with a single mother can be quite a change, especially if you've never ventured into this territory before. It's great that you are thinking ahead and trying to formulate a plan to assure that things go as smoothly as possible.

I would basically ask her exactly what you asked me. Tell her that you've never dated a woman with children before and you'd like her perspective on how to best make it work. You can ask about her experiences dating men who don't have children; if she's been dating for a while, she's likely been with some guys who've handled the situation well and some who have found that it wasn't for them. What does she think makes the difference? If you have specific concerns, go ahead and voice them. For instance, you may have questions about the children's father, or how she feels about introducing her children to her dates. If these things are on your mind, it's more than okay to ask. I've found that one of the best things about dating people with kids is that because they've experienced more in life than your average person, they're typically more willing to put everything on the table and be open and honest from the beginning.

When should you begin this dialogue? That kind of depends on how your relationship progresses and her openness about her family and dating situations. If things start off strong and she appears to be very open about her lifestyle, it may be okay to have these conversations as early as the first date. If things progress a little more gradually, perhaps the third or fourth dates feel better. It's different in every situation and really comes down to what feels right to you.

Telling her that you've never been in this situation and asking for her help also shows her your level of maturity and dedication to making a relationship work--both very good things to a woman whose first priority is providing a safe and stable environment for her children. Good luck!

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