The Ultimate Guide to Dating as a Single Mom

Dating as a Single Mom Motivation

You are learning about dating as a single mom…Congratulations! Why are congratulations in order?

My congratulations, cheers, and hurrah go to you, mama, because you have decided to date! Here, we are big on celebrating yourself because you deserve it! And it takes a lot to get out there again, usually after years of being single. So pat yourself on the back, do a stretch, have a chocolate because you are in for the ride of your life!

You're going to want to read all this juicy info because in this article I share my most important tip for saving time while dating as a single mom! And we all could use more time, right?

Getting Ready to Date Again As A Single Mom

First things, first, are you ready to date again? Let's see…

Are you over your ex?

Have you gotten over your ex? Do you still want to be with your ex? If he were to call and say that he had changed x, y, z and was willing to do x, y, z, would you want to take him back? If you think he seriously has worked on the things that were a problem, it might be worth investigating. But, if you're like, Nah, I've heard this all before and you won't put up with anymore bullsh$# then you are over him!

Therapy for Single Mothers

Have you had therapy? I recommend it for most single moms. No, lady, you're probably not an exception. Sorry, not sorry. How else are you going to do something different in your next relationship? Make sure you get a good one, someone you click with and can tell anything to. A great therapist is one that you can tell anything to, without judgement. And they help you come to your own conclusions, not tell you what to do in your life. Don't feel frustrated if the first one you see isn't right for you; that is often the case.

Repeating Relationship Patterns

Have you realized what your blocks are or what was your problem in past relationships? Even if the man had many problems, you at least had the problem of picking him and putting up with him. So what's that about? Do you see a recurring theme or pattern in your relationships?

Single mom thinks about relationship patterns to get ready for dating.
Photo by John Diez from Pexels

How to Stop Relationship Patterns

Are you working on the above-mentioned blocks, patterns, etc.? This can start with the therapy. Also, this could be journaling, meditating, etc. Really, there is a whole lot that goes into this and it is too much to go into here. You don't have to be perfect at this but must be working on it.

Know What you Want in a Relationship as a Single Mom

Take some time in your therapy to not just talk about past relationships but about the future. Think about the things you want in a relationship. Or the qualities do you want in a man. What do you want the relationship to look like? How will you spend your time together? Maybe you are a big outdoors-y adventurer and spend most weekends hiking a mountain. If you are, it would be hard to sustain a relationship with someone who loves binge watching shows all weekend long. Not saying either one is better but that they are different.

Childcare for Single Moms

You want to make sure you have options for childcare, so you can actually go on those dates. Whether it is your mom, your sister, your friend, or a sitter, you gotta line that up and know you can get out! For the most part, you should not bring your child with you on dates. The exception to that might be if you are in an exclusive relationship and serious with a man, then you may bring your child on some dates, especially if they are family-friendly, like the zoo.

Your Social Calendar for Dating as a Single Mom

Planning in a calendar to get ready for dating as a single mom.
Photo by Sam Lion from Pexels

Figure out what days/nights of the week work best for you to go out. Is there a night that your favorite sitter is usually available? Then, make that night date night every week! It is also good to have a second option of days, in case your suitor can't make it on your first preference. So fill out your planner or calendar and make dating a priority!

If you have made it through this list and checked off these items, or are actively working on them, then you are most likely ready to date!

How to Date as a Single Mom

Where to Meet Men as a Single Mom

Hey, it is a digital age so where do you think the best place to meet men is at? You guessed it, online! There are so many online dating sites and apps, I can't even keep track of them all. But, I will write a future post about my fave ones. And, when dating as a single mom, this is a great time-saver, since all the men are on your phone or laptop!

The Basics of Online Dating for Single Moms


First thing to remember, visuals are the most important thing when it comes to online dating. The. Most. Important. Thing. It doesn't matter if you have a heart of gold, if your pictures suck, then you won't get very many matches. Notice I didn't say if you aren't attractive. Look, everyone has a different thing that they find attractive. So no matter what you look like, you're great. The key is in having fabulous pictures that highlight your best features.

Tips for great pictures:

Smile and wear your best colors, clothes that show your best features. Try to take them outside if you can. Avoid selfies! Even though you are dating as a single mom, do not have your children in your pictures.

Dating as a single mom requires good pictures like this one!
I mean, look how cute this pic is? It is way more swipe-able than a selfie in a bathroom!

The Online Dating Profile

If you're new to dating as a single mom, you may not know how online dating works. First, there is the profile. This deserves a whole separate post, which I will do in the future. The profile depends on the type of site or app that you are using. Some sites have long profiles, some have only a few sentences, some use quizzes to match you, etc.

How to Have a Great Online Dating Profile When Dating as a Single Mom:

First, be positive! And say what you want in a man, not what you don't want (that's negative). Give him a glimpse into what your life is like, what activities you do, etc. You must mention at least once that you are a mom! This is crucial information! I know talking to some guys after reading their profile, which didn't say that they are a dad, I was kinda confused why they left it out. I don't think it's bad that a guy has kids but if he doesn't mention it in the profile, it makes it seem like they are not important to him or he is ashamed.

Conversation Starters to Use Online

Great, you matched or he liked you! Now, you get to decide if you want to send the first message. It really doesn't matter if the man or woman sends the first message. The man will never remember who sent it first. So, if you like him, shoot your shot!

Some things to remember: again, keep being positive! Talk about interesting things in his profile, ask him about a picture, etc. In general, it is better to ask an open-ended question to keep him engaged. Think about it, if you were messaging a stranger, it would be helpful to have a question to answer. Also, it shows that you are interested in him and his life!

Get off the App

You must try, within one or two messages, to mention a way to get off the app. This can be mentioning having a phone call or video call. Look, it is like being a kid in a candy store while being in the dating app or site. There are so many other people to look at, like, match, message, etc. that it is too distracting! You want him to focus on your and get to know you, without a bunch of virtual women around. That's why it is crucial to get him off the app in some capacity as soon as possible. Really really try to schedule your phone or video call (more on that below) before getting off the app, so you don't end up in texting purgatory.

Texting Purgatory

My definition of Texting Purgatory: the endless state of texting a guy random info about your life and trying to set up an actual phone call but not getting anywhere until you die. And eventually one of you becomes a ghost. And we all know about ghosting! Also, if you are texting a man a lot every day and have never actually talked to or met this man, it lends a false sense of intimacy. Listen, if a guy deflects attempts to set-up a phone or video call, he is not that interested in a real-life relationship. Stop texting the dude and move on. He is not even worth your texting time.

The Most Important Tip to Save Single Moms Time While Dating: Phone Call or Video Call

Here it is, the most important thing that will save single moms time… is doing a phone call or video call prior to an in-person date. This is so critical: you get to hear his voice and possibly see his face, if doing a video call. You get a sense of his vibe.

There have been a few guys that I talked to on the phone that were so incredibly negative, I couldn't imagine spending an hour or an evening in their company! I'm so glad I did a phone call first so I didn't spend what precious time I have on an in-person date that would've gone nowhere!

For single moms, this is ideal, you get to talk on the phone while your kid is asleep, on the tablet, or whatever. This means you save money on a babysitter! Plus you don't have to take time to get dolled up, unless doing a video call.

Which is Better for Dating as a Single Mom: Phone call or Video call?

This is usually a matter of preference or what the man asks as well but I have found a few things to consider. The thing is, I found that if I was doing the call after I put my daughter to bed, I learned it would be best to do a phone call. The reason being, I would get so relaxed after doing lullabies with my daughter, that my face would look super tired and it seemed like I wasn't interested in the guy. I think I turned off a few men from trying to push through on that video call late at night. It is much easier to make your voice sound excited than make those eyes look bright! So get some pep in your voice and call that guy tonight!

But, if you can get your kid interested in some safe games on the tablet for about 20 minutes, you can do a video call while they are still awake! And, hopefully, you will look awake too! If doing a video call, you should at least have some make-up on and a cute top on. From the waist up, it should look like you're going on a casual date.

Dating as a single mom requires having phone calls before going out in person on a date.
Photo by SHVETS production from Pexels

Safety in Dating as a Single Mom

You have to be careful these days because creeps are out there. Remember, you will have some verification of what he's about, after a phone or video call prior to that date. Before the date, let a friend know the man's name and send a pic of him to your friend. Also, tell your friend where you are going, the timeframe for the date, and other identifying info (town where the guy lives, where he works, etc.). If possible, arrange for the friend to call you during the date. You must have the first date in a public place. Do not get in his car at any time during the date, even at the end when you think he's a “nice guy.”

The First In-person Date

The first date is just a way to determine if you want a second date. It should be casual and fun. Simply, coffee, ice cream, lunch, dessert, walk in a public place, etc. You can decide to go on a second date because you didn't notice any red flags.

Red Flags to Notice On a Date

Here are a list of red flags that my friends or I have seen on dates. Here is another article about red flags.

  • He's significantly late and doesn't let you know
  • bringing up exes during a first date
  • asking you about your exes during a first date
  • explaining that past girlfriends were all at fault, “crazy,” “gold-digger”, couldn't be trusted, etc.
  • He has some sob story for something in his life, and he brings this up on a first date.
  • saying that he's only met crazy women online and that you are the normal one and what a relief
  • asking if you are seeing other men (especially if this is a first date, girl, run!)
  • telling you that he is not seeing other women (this is usually a lie)
  • asking you to tell horrible stories of men you have met online (even if you have them, don't do it)
  • trying to get physical too fast (i.e. grabs your breasts in a public place)
  • pries too much into what other things you are doing that day or week (he has no right to ask what you are doing and with whom)
  • saying he thinks you are the woman he has been waiting for his whole life
  • not respecting your dietary needs, whatever they may be (this shows a lack of respect for you as a person and is a big no-no)
  • Related to that, he doesn't let you eat
  • telling “funny” stories about how he screwed over someone, or messed with some ones head, and is very proud of it
A grumpy man who may be full of red flags.
Photo by Andrea Piacquadio from Pexels

How to Schedule a Second Date

The best time to schedule a second date is at the end of the first one! At the end of your date, tell him you had a great time and would love to see him again! If he agrees that he would like to go out again, tell him that you are available next Wednesday or Thursday night (or whichever day you are free) and which would work? Hopefully he can schedule it with you right then and there. This is why it's so helpful for single moms to have a calendar created and know when you have access to a babysitter.

When to Go on Second Date When You're a Single Mom

If you don't notice any of the above red flags, plus your gut isn't picking up on something that I didn't list, you may proceed forth on a second date. The second date can be anytime you both are free! Please don't subscribe to those antiquated rules of you must go on the second date within 3 to 5 days of the first date and only if it is a new moon or whatever. You are a mom and need to do the date when you can! Also, don't feel scared to be really open and tell him when you are free. If he hasn't set up an exact day for the date, but you know your ex husband will have the kids on Friday, tell him you are free to go out on Friday!

Should you Date Multiple Guys at Once?

Yes! I can practically guarantee that the man is dating/talking to more than one woman at once. Somebody once said, Have a pair and a spare. So ideally you should be talking to/going on dates with at least 3 men at once. As a mom, I know I get really tired and overwhelmed with life with kids, let alone talking to multiple men. So I usually can only handle 3-5 men at once. But see how you feel and what your limit is. At least talk to 2 guys at once!

How Long to Date Before Being Exclusive

A single mom has found her boyfriend after successfully dating!
Photo by Sofi from Pexels

Ideally, you have gone out a handful of times before being exclusive. This can be over the course of about 4-6 weeks, or a little longer if you are dating 5 men at a time. But when you feel ready, you can discuss the topic of a relationship with one man. Don't worry about rejection: if he has gone out with you multiple times, most likely he is highly considering you as girlfriend material!

When to Introduce your Children to Your Boyfriend

This is different for every mom and child situation. You have to do what you feel comfortable with. Ideally, you would get through the first few months of dating exclusively to see if you really like this guy before introducing him to your child.

Congratulations! You have successfully navigated dating as a single mom! Now go have some fun!