Advice on dating a single mother
Don’t assume she’s not free when her kids are home. If you’re interested and want to see her, ask her out. They have a dad, regardless of whether he is in the picture, in the can, or in and out of the psych hospital. But if you explicitly ask these details on the first or second date you will appear reluctant about dating a woman with kids.
If she prefers not to go out when her kids are home, or doesn’t like to hire a babysitter on school nights, she’ll tell you. If you’re out and she is paying for a sitter it is really nice if you get the check. Which you may be – but if you ask too fast, she will know.
I went out with a girlfriend in Montclair, NJ, to a fun place called Just Jakes. It was a little deceiving, sure, but I thought telling the guys I was a single mom would influence their answers—and I wanted raw thoughts.
It may appear effortless, but effortless actually takes more effort.
Respect that it’s a big deal when she introduces you to her kids.
When I found myself in the midst of a divorce and navigating a new dating world -- this time as a single mother -- it dawned on me that any experience garnered in my former incarnation as a single woman had to be thrown out the window.
Dating-as-a-divorced-mother was an entirely new game, one whose rules -- despite my eagerness to learn them -- remained steadfastly mysterious.
If you don’t ask her out — no matter how innocuous or considerate the reason — she will assume you don’t want to see her. Leave the ask to the last minute, she has to scramble to find a sitter and that’s really uncool. This shows interest in one of the most important things in her life. Sounds cliche’, but I always appreciate it when a guy goes on about how much he adores his niece, or spends time with a friend’s baby. This isn’t necessary, and especially after you have been involved for a while you will likely sort out the who-pays-when conundrum. But she wants to feel like you’re interested in her in every part of her womanhood — including motherhood. If it has been more than a few months, or things get very serious very quickly, and she hasn’t brought up introducing the kids, bring it up.