This guy needs your advice about dating a single mom

by singlemomseeking on March 12, 2008

boy.jpg E. is a single, 33-year-old man who recently started dating a single mom with a two-year-old son. This is new territory for him, and he wrote in yesterday to say that he’d really appreciate some advice.

First, E., thanks for being bold and reaching out. Here goes:

E. met this 32-year-old single mom just two weeks ago on Eharmony. I know that many of your single mama readers will be up in arms, but this single mom brought her two-year-old son on their first date.

“The night of our first date, her sitter called to cancel an hour before our date,” E. writes. “Rather than postponing, I asked if she wanted to bring her son along.”

He explained to her that he’s an active uncle with his four nephews and three nieces, and that “I would be completely ok with her having her son at the restaurant as long as she was.”

So, she brought her kid along — he “was great bridge in getting over the nerves of meeting her for the first time” — and they’ve been seeing each other since.

This single guy wants to know: “Do you have any tips or advice for a single man with no kids who’s dating a mother of a two-year-old?”

He ends with: “I look forward to any advice you and your readers have. I’m treading on new ground here and would like to avoid any land mines. LOL!”

No doubt, many of you will tell E. that suggesting she bring her son was a big No-No. That’s done, let’s refrain from judging. In the meantime, the two have spent a lot of time together, “just the two of us. I have seen her son since the first date, but he has not joined us on any of our adventures together.”

Lastly, his single mom girlfriend has been divorced for six months. E. adds that “the father is involved but not very active. He has seen his son a handful of times in the last six months.”

Take it away single moms:

Should E. offer to pay for a sitter when they go out? Should he be jumping into make dinner?

What kind of advice would you give E. about respecting this mom’s space… and making boundaries?

Is it okay for this mom, say, to sneak E. into her home… after her son is asleep? Or, should they take it very slow?

Photo courtesy of RED Visual Group

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{ 13 comments… read them below or add one }

Ray July 8, 2012 at 8:07 pm

I think one has to look ahead and ask about how far this relationship is expected to go. Normally when you are dating a woman with no kids, this is not a big issue. However, when you date a woman with kids, you kinda have to cut to the chase: How soon is she looking to get married? I don’t know of a single mother who is not thinking about this at some point early on in a relationship (which is reasonable). However, you have to realize what you are contending with and that you have to consider that you may never be a traditional spouse. You’ll have to be the guy with the big heart who “accepts the kids,” but will the kids accept you, and if they don’t…where will the mother come down. Consider the possibility that you MAY never be her first priority. Your values regarding child rearing will not be primary with “HER KIDS,” and she’ll remind you of that if you forget your place. I am not bashing or promoting this kind of arrangement, but you have to have a “big boy/big girl” conversation about where this is going sooner than you would with a woman without kids, and it should not be one sided based on her needs and wants only. These relationships can progress quickly if the man is a good prospect. But remember this: She will unapologetically demand that you make her and her kids you primary priority if you marry her. You should demand the same of you, if she is unwilling to do that then you should pass on the relationship early before expectations get out-of -hand.


singlemomseeking March 20, 2008 at 6:57 pm

E: I’m so glad that these Super Single Parents helped you out! It’s so sweet that you went to the zoo.

Computer Dad: well said about responsibilities. Wow, so true.

Kim: Yes, here’s to thoughtful single men like E!


E March 20, 2008 at 8:08 am

I would like to take this time to thank all of you who have left some incredible advice and suggestions. I was a little skeptical at first to ask Rachel for help and now I’m very glad I did!!

Everything is going well with us.

We went to the zoo over the weekend just the 2 of us while a friend of the family watched her son for a couple of hours. I haven’t been to the zoo since I was 7!!

Thanks again and keep the suggestions coming.



Crazy Computer Dad March 18, 2008 at 2:18 am

E. I don’t know that there are any hard and fast rules to go by. There are many varying circumstances and situations around each person. Some things to keep in mind is that as a single person without a child you may spend 8 hrs or so a day at work, but after work you can go workout, hang out with friends or co-workers, catch a movie, watch TV, volunteer work, etc. You probably have few actual responsibilities outside of work. A single parent doesn’t have that time. After work for them means coming home to another few hours of responsibilities in caring for their child, spending time with them etc. That person may get an hour or two a night to themselves before collapsing and having to do it again the next day. The weekends are filled with responsibilities for the child as well (depending on how involved the other parent is they may get some weekends off here and there). In the spare time that she has she probably wants to spend a lot of it with you. She probably wants to spend some time with her friends, and she needs some time to herself. It is the last thing that is likely to suffer through the first part of any relationship because there is a big desire to please and be with the new person. That is eventually going to put a big strain on everything else, including her relationship with her child. It is extremely tough to balance. While you have a lot of time to yourself, she does not, so make sure that when she asks (and like most people she may not know exactly how to ask for it…at least I know that don’t) give her some time and space to herself. No need to try and rush things with her child, and definitely don’t try to buy the child’s affection. A bond will form with the child over time if you are seriously dating the parent. Each child is different. Pay attention to them, be responsive and involved. You may be surprised how perceptive children can be and how they know they are being ignored when an adult says “Wow, that’s nice” to something that have done or created. Ask questions, show interest, and try to really appreciate what they did. All of us like to feel appreciated right?


Kim March 17, 2008 at 4:50 am

Well this makes me feel optimistic when I hear about men like E.
My two cents would be: Take things slowly always recognizing that as a single mom she has a lot on her plate and anyone with whom she gets involved with will need PATIENCE AND UNDERSTANDING.
Otherwise, just be honest and realize that she probably isn’t looking for any drama in her life…. so always keep it real.
I don’t like the idea of paying for a sitter for her kid…. that is a bit too close to a ‘dad’ who pays for the sitter so he and wife can go out. Too much involvement, too fast.


singlemomseeking March 14, 2008 at 2:39 pm

Ms. Single Mama: Ah ha, you ARE the single mom of a toddler, that’s right! You would be the perfect go-to woman for this.

Lady Fox and Leslie: Thanks for reminding E. not to take things personally if she’s feeling exhausted.

Amy: Oh, girl, you are so right on! Why didn’t I think of that? Ask her what she wants/needs… sit and and listen. Thanks.

Dr. Leah: Thanks for reminding E. that this mama needs to make time and space for her friends, family… and, of course, sleep!


Ms. Single Mama March 14, 2008 at 9:37 am

I could write a lot about this … and have. So guys – check out my tips on “How to Date a Single Mom here:

And single moms, here are your tips:

Thanks Rachel for bringing attention to this!!!

Just last night my boyfriend was over (he’s only over two days a week now). He was leaning in for a kiss and I was putting the cap on Ben’s sippy cup when all of the milk splashed all over us! So the best tip I can give is – patience! Ha!


ladyfox March 14, 2008 at 7:38 am

I have only gone on one time dates never really dated just one yet, but yes communication from the start is good. Taking things slow is good and keep in mind that if she says no to a date …..its not you, maybe shes to beat to get all glammed up. So later on yeah why not offer to pay the sitter for a special day like a birthday or big date. Also a late night movie at home is always good.


A. March 13, 2008 at 11:37 am

Above all—ask her—ask her what she wants from this relationship. The more you two communicate—the clearer the message will be. Every single mom out there is coming from a different place–and we each want different things–so, the only real way you’ll know is by asking her—and assuming that you both have good communication skills, she’ll be able to tell you…and you tell her what you want as well—then it goes from there….


Dr. Leah March 13, 2008 at 9:59 am

Leslie: Wow! I love what you said. If a SM shared a “typical day” or just her worries of the moment, most guys would feel overwhelmed by the “fix-it” urge. A sympathetic non-judgmental ear would just be so welcome. Thanks so much! Dr. Leah


Leslie March 13, 2008 at 6:13 am

I’d love to know how someone has time to fit in that much time together in a couple weeks – I’m jealous!

Looking back I wish I’d taken advantage of dating when mine was that age, it does give you plenty of time after they’re asleep or on a fun night at grandma’s. Mine never really cared what I was doing if he was having fun so it does afford you a little freedom without questions.

But I’d be wary of getting too involved in their everyday life too soon, in a few months things may feel different and this little guy will already enjoy having you around even as a buddy. Everyone is different but I’d guess mom’s going to need her space too, and totally agree with the above, needs to keep up those friend bonds with those who probably have been or will be lifesavers.

I’m never sure how or when to “break someone in” on how single mom life works. (Blogs are good for that though huh) When to be really honest about the financial struggles, stress, worries. Remember that if she does share her “real” day, don’t worry about trying to fix things, just listen. And if she doesn’t want to share it, remember life may still be tough but she’d rather forget it and enjoy time with you. Neither reflects on how she feels about you or what depth she wants the relationship to go.


Dr. Leah March 13, 2008 at 4:53 am

The whole “takes a village ” thing has been so overused, but, in this case, there’s a useful take away message. A two year old does give some latitude for now for overnights, definitely, but, since the child’s father doesn’t sound like he is making much of a consistent effort, this SM may want to keep in mind the value of having guy “friends only” in her life. Until she is really absolutely sure that this relationship has lasting staying power, she does not want this guy to be the only constant man in her child’s life. Advice to him: Be mindful of her needs to keep her posse intact, and that especially includes guy friends.

Best of luck!


Angie March 13, 2008 at 3:50 am

If this single mom (sm) has only six months under her belt, this dating as a parent thing is new to her too. In my experience, sm will be getting TONS of advice – whether solicited or not…and mostly it will be contradictory. Sm will want to do what’s best for her child, so she may behave a little bi-polar in her relationship. One minute wanting to spend lots of time with E, the next wanting to only see him after her son is tucked away in bed. E needs to have patience as she adjusts, knowing up front she’s not having trouble with him — only with fitting him into her and her sons life.

Since the son is only two, I don’t think late nights will be a problem…but for sm it’s a one time luxury. After her son grows a year or two she’ll be cut off from overnights!

It’s a tough road for both sides, I hope it works out!

Wishing Luck!


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