I'll babysit for you!* Of course this is something any single mom would love to hear, but it's the follow-through that really counts. Don't sporadically offer to babysit, because it puts the single mom in a place where she has to ask for help—and most single moms thrive on independence and a I-got-this attitude (I do!). Instead, name a time and day. This tells the single mom you mean business and she'll be more likely to plan a date night. There's nothing worse than planning a date and finding out you have no one to babysit.
OMG Have you tried online dating? YES! Chances are she and every other breathing single woman have tried online freakin dating. There's nothing groundbreaking about online dating, people. I mean, it's basically old news. Instead of throwing her online, throw her a man. You know someone. Your husband knows someone. Someone knows someone your single mom friend can go on a single, uno, one date with—it's not like you're setting her up for a marriage proposal (and if it turns into that, you rule!) Even if it's not a match made in romance heaven, it's a night out for her and it shows you care. That's what friends are for!
You're lucky to be alone because my husband is xyz! No, no, no. A single mom is not lucky to be alone and it's certainly easy for you to tell her so … then rest your head next to your man after the feeling of disgust, anger, or xyz passes. Don't project your relationship snafus onto a single mom who is juggling a child, work, home, (possibly) deadbeat father, oh and dating. It's just not cool. (Yes, she's your friend and wants to hear about your hiccups—but they're not about her relationship status—to make you feel better.)
Maybe you should give him another try. Whether you're talking about her child's father, an ex-boyfriend, or a former lover, if she needs to give him another try, then there's a reason they're no longer together and she's trying to meet new people. Don't discourage. It's easy to fall back on the past because it's what we know (trust me, it's easy for a single mom with no time to date to fall back on an ex because they enjoy sushi dates and well, he's good in bed, but it's not healthy). Encourage her to find someone better. Besides if this ex is meant to be in her life … he'll find his way back.
Perhaps you should take a break from dating. A lot of the time, single moms date to get out and have adult conversation. It's an escape into a world that doesn't revolve around being a 24/7 parent-themed circus. She's dating for connection, friendship, and an all around break from life.
Do you have anything to add to this list?