My first post, How to Date a Single Mom, Part 1 is a nice list of what men can expect when dating a single mom. But it lacks detail. 

And of all of the e-mails I receive, the most common are e-mails from men who have fallen for single moms and the theme question is this:

“I can’t tell if she likes me or if she’s blowing me off. If I go by your advice I should be patient and expect her to keep me at a distance but how can I tell if she’s just not that into me?”

My advice is always to ask her point blank (rip that band aid). But that is probably THE scariest bit of advice I can give them. Men don’t like talking about things – especially the “Do you like me, I like you thing.” So, fellas, here’s some more advice. If you can’t tell clearly that she’s into you, there’s a good chance she’s not but when you’re dating a single mom there’s also a chance she’s keeping you at arms length, afraid to fall. Why? Because she’s been here before, she’s seen the likes of you and even if her heart is telling her to dive right in her mind is screaming “Watch Out”. Can you blame her? So how do you tell if a single mom likes you or not?

I think the more fitting advice in your situation is this – stop worrying about whether or not she likes you and get busy – make her like you, earn her trust and her love.

How to Win a Single Mom’s Trust and Her Heart

1. Ask her how she is doing. First and foremost, on a date, at the beginning of a phone conversation… always ask her how she is doing. This may seem obvious but there are so many men I’ve dated who fail to ask me how I’m doing. (I know, atrocious, that’s why I’m not dating them anymore). The men who ask, wait for an answer, listen to the answer and then respond with encouraging words are the men who catch my attention.

2. Ask her about the kids. Don’t force this. Be genuine. But ask about her children. She may assume you want nothing to do with her little ones, but asking proves that you do want to learn more about that side of her life.

3. Always pay for everything on your dates. She’s paying for a sitter, the least you can do is foot 100% of the bill. By the third date if she’s insisting on paying, split the bill. 

4. Surprise her. This is universal for women but with single moms you can’t leave flowers on the doorstep (the kids might see them). Instead surprise her with unexpected date plans or leave a note in her mailbox with a gift certificate to a spa or salon. Surprising her with a thoughtful gift or date proves that you care about her. The theme here is going the extra mile to earn her trust. 

5. Don’t unload your crap on us. The last thing a single mom needs is a man she perceives as another person she’ll have to take care of, emotionally or financially. If you’re not together on these two fronts you may not stand a chance. 

6. If you’re lucky enough to get into the house… this will likely happen on a night when the kids are at their father’s or after you’ve been dating for a few months. But if you do get your foot in the door, literally, HELP OUT. Clean up, do the dishes – even if she insists that you stop (unless it’s multiple times and she’s pissed for some reason) but get your hands dirty. WARNING: Do not criticize the state of her house. Imagine working a full-time job, child-rearing, doing the laundry, the dishes AND keeping the house at maximum tidiness. And she probably cleaned up before you came over. 

7. Get her to relax. One of THE toughest things for us single moms is actually relaxing. I personally have to go to great lengths to unwind. If a man really wants to win me over he’s got to figure out how to put me at ease, physically and mentally. If you’re on a date – get her on a dance floor, or walk to the next bar – the physical activity will help her to loosen up. If you’re at her house and you’re cuddling – give her a back rub or light some candles. 

8. Say thank you. If it’s your first date or seventh, always say thank you. Remember that to see you she had to clean her house for the sitter, hire the sitter, pick out what to wear and all of this while taking care of the kids. 

9. Plan the dates. I can’t speak for all of the single mothers out there, but the men who take the time to plan a date out for us win major points. They realize I don’t want another thing to worry about. The key is to make the night and her encounters with you effortless on her part. 

10. Flowers and sweet nothings. As always, bring flowers when you pick her up. I’m a big flower girl. VERY obvious again, yet so uncommon. As for the sweet nothings, you’re supposed to whisper those in her ear, send them via text or e-mail. 

Good luck! Single moms reading – chime in and add to my list to help these guys out!

And my other How to Date a Single Mom posts:

How to Date a Single Mom, Part 1: The original, a very nice list on how to date a single mom.

How to Date a Single Mom, Part 2: What to tell a man dating a single mom?

How to Date a Single Mom, Part 3: Hear from a man who spent 5 days with Benjamin and I.

How to Date a Single Mom, Part 4: Take your vitamins.

And you might want to read this:

Can Single Moms Really Fall in Love?

Related posts:

1. How to Date a Single Mom, Part 4
2. How to Date a Single Mom, Part 2
3. How to Date a Single Mom, Part 3