I go out with single dads and childless men alike, and some of the latter admit (while others appear) to be uncertain about the logistics of dating single moms.
Here are my tips for men who want to date a single mom:
Don’t assume she’s not free when her kids are home. Women like to be asked out. If you’re interested and want to see her, ask her out. 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 don’t ask her out — no matter how innocuous or considerate the reason — she will assume you don’t want to see her.
Ask her out ASAP. Leave the ask to the last minute, she has to scramble to find a sitter and that’s really uncool. Plus, it tells her (and any other woman, for that matter) that she was your Plan B for the evening. Which she may be. But if you really want to see her, give her plenty of time to sort out her schedule.
Ask about her kids. She won’t assume you’re a pedophile. This shows interest in one of the most important things in her life. In fact, if you DON’T appear interested in her family she’ll think that you’re not into kids.
Let her know you love kids. Assuming it’s true. 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. When a guy laughs at my funny-kid story, or is sympathetic about my mom worries, I’m in.
Don’t assume she is down and out. Maybe she is broke, but don’t assume. It will piss her off.
Don’t assume her kids need a new dad. They have a dad, regardless of whether he is in the picture, in the can, or in and out of the psych hospital.
If you’re out and she is paying for a sitter it is really nice if you get the check. 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 if you tend to take turns picking up the bill, but she sometimes rearranges her life to get out of the house and pays for a babysitter so she can spend time with you, acknowledge that.
“You look great for a mom.” That. Never say that.
Don’t ask to come up when her kid are asleep. Just don’t.
Hang tight on asking about visitation schedules. Of course you want to know when she is free, if she has the kids all the time and whether the dad is involved. But if you explicitly ask these details on the first or second date you will appear reluctant about dating a woman with kids. Which you may be – but if you ask too fast, she will know. But she wants to feel like you’re interested in her in every part of her womanhood — including motherhood.
Wait for her to bring up introducing the kids.
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.
Know that when she invites you over, it is more work for her than when you invite her over. Yes, moms are really efficient and they’re used to doing a lot of cooking and cleaning. But if a single mom invites you over for dinner — whether a romantic evening for two, or with her kids — she had to clean up a whole lot of Legos and finger paint and sting cheese wrappers, and wrangles in an extra trip to the market and wine store to make it happen. It may appear effortless, but effortless actually takes more effort.
Respect that it’s a big deal when she introduces you to her kids. She is opening up her life and her whole family’s life to you. Treat this gesture accordingly.
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