Dear unknown man who is thinking about taking out a single mom,

The following do’s and don’ts have been personally experienced. You might find them helpful. You might find them offensive. I’m just one single mom out there who chose to write about the things she liked and didn’t like on her first dates. Of course, most of this won’t be an issue if a relationship develops, but as for a first date

1.    DO offer to pay for her sitter. Before you drop your jaw in disgust, I do fully understand that this might be deemed super high maintenance. Here’s the thing: She has said, “yes” to going out with you which means she likes you enough to work all day, come home, stay off the couch, get dressed up, wear make up past 7:30 pm and then pay someone to come keep her kids in order to spend time with you. Way to go dude! Count this as a major win! It takes a really great guy for me to do all of that. Now, concerning the babysitting, this will most likely cost around $30 – $40 for the evening. The going rate these days is $10 an hour. Most guys don’t think about offering to pay for this, which is completely fine, as this is not at all their responsibility. BUT! Several years ago, I had a man offer to pay for my sitter (the only guy to ever do so) and it took me so incredibly off guard…in the most wonderful way you could ever imagine. Your date might politely decline, (I did) but nothing screams, “I’ll take care of you AND your family” like footing the bill for the sitter on your date. This will show her you are thinking about all aspects of the evening, including making this night as easy on her as possible. For her, this will go far beyond the normal thoughtfulness. She’ll be impressed, yes, but also she will feel very, very cared for.

2.    DO stand up any time she leaves or returns to the table. I teach at a private Christian school and it is a policy at our campus for a class to stand when a visitor enters the room. Last month I had to walk into a class of seniors and they all stood as I walked in. Oh my word. I felt like I had just stepped off Air Force One, and was being saluted by dozens of marines. I think I actually bowed involuntarily because of the feeling of humility that came over me.  If your date is indeed a single mom, there has most likely been a man in her past that wasn’t super respectful to her, so while she probably already has you on a small pedestal simply from your normal way of treating her, going above that norm would be a true luxury. Stand up when she leaves and stand up when she returns. She’ll highly respect you for it.

3.    DO make sure to ask a few questions about her kid/kids. (As if #1 wasn’t high maintenance enough, I’m going to throw this in there too:  DON’t ask too few questions, she will assume you don’t care. DON’T ask too many questions, she’ll be weirded out by your abnormal interest. I would suggest 3-4 questions and then move on.) These are the little beings that she prays for every day. She has stayed up countless hours with them on sick nights, nights with bad dreams, and nights with awful bathroom accidents. She thinks about them with every decision she makes: vacations, budgeting, which house to buy, what schools to attend, her work hours, what food to purchase, everything. They changed every perspective she had when they were born. They are a massive piece of her life.  She’ll thank you for asking about them.

4.    DO always, always, always pay for dinner. No exceptions. I was out with a guy one time and he said, “I can’t pay for you and Wes. I don’t have the money.” I didn’t mind at all! If anyone understands a budget, I certainly do. Then, one hour later, we ran a few errands together and he bought quite a bit of dollars worth of oil for his dirt bike. It was over three times the amount our meal was. There is a difference between having a hard time financially and just not wanting to pay for her and her kid. Decide beforehand if she is worth it. Once you’ve decided she is worth taking to dinner, please pay for it. She might offer to pay, (I do) but hear me…DECLINE and INSIST. I don’t care if she makes quadruple the amount of money as you. Pay for the dang dinner. She’ll truly appreciate it.

5.    DON’T press her to meet her kid/kids. Let her decide when the time is right. Some moms don’t want to introduce their kids to their significant others for a very long time. Give her space. Enjoy getting to know her for the time being. She’ll be grateful for your patience.

6.    DO be open and kind if she brings her kid/kids on your date. Every mom is different. Some moms bring their kids on every date so that the man will know what real life is like. If this is the case, then enjoy her and her tribe. It’s completely okay if you decide that this isn’t for you, but for the date’s sake, have as much fun as you can. She’ll love your compassion.

7.    DON’T say, “I’ve never dated a single mom before. In the past, I’ve been closed off to the idea, so I’m trying to be more open about it.” I had a conversation with a man who said this to me and I immediately translated that to, “I never wanted a woman with kids, but now that I’m older there’s no one left, so I’m having to date moms and I hate it.” She personally won’t like hearing it (I wanted to punch the guy in the throat), but she will also feel really defensive for her small cubs. You don’t want to finish your meal with a sharp-clawed grizzly.

8.     DO say, “You are a great mom. I admire all that you do for your kids.” Right now, she is doing this on her own and even though she may have found her groove and is doing pretty alright in life, compliments on her motherhood are not only welcome, they will be treasured by her for eons of time. You can never go wrong by speaking of her motherhood kindly. You’ll see her face light up and beam as if she has just been given the Congressional Medal of Honor. If you’re willing, compliment her motherhood as much as you can. It will give her pounds and pounds of refreshment.    

9.    DO walk her to the door at the end of the date. Do not be the guy who offers “the awkward walk back”.  No girl, I repeat, NO GIRL wants her date to watch from the car as she walks to the door, especially on a first date.  So many unsettling thoughts will race through her mind in the 6 seconds it takes her to get to the front door knob. Where’s that dude looking right now? Is he driving off already? Is he watching me? What if I fall down? I’m so ready to get these heels off. Why is he still in the driveway?  Do I turn around? I can’t wait to wash my face. If I do turn around, do I wave or smile or…? UGH. The whole thing is eerie and awkward, and flustering and awkward and worrisome and awkward and also the complete opposite of chivalrous. For all that is noble, just walk her to the door. 

Here’s to first dates!

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