The tips and tricks I’ve learned and would do even without kids
Dating as a single mom is one of the most emotionally complex things I have ever done because it brought up a lot of my preconceived ideas about mothers and sex, and my conditioned beliefs around what was “appropriate” for us in romantic relationships, especially when it comes to our children. Plus, I felt like an insecure teenager all over again and afraid to admit that in my thirty-something adult body. I needed solid boundaries, a lot of permission, my inner guidance, and someone with experience to show me the way.
In case you needed to hear this like I did, mothers deserve the same opportunity to have full, satisfying sex and dating lives, regardless of their relationship status. This is for you if you’re single and dating more casually, if you’re committed to someone romantically, or if you’ve been married for decades. This topic doesn’t become permissible only once you’re in a committed relationship.
So if I’m a mom and I want to actively date in a way that makes me feel free, optimistic, and satisfied, what does that look like? Here are my tips.
Just a heads up: I am a mom with 75% custody of my two children, ages 7 and 4. They have a great dad with whom I have an amicable and civil relationship. We have our struggles, but we’ve both worked very hard to get to the relatively positive place we are in. I’ll do my best to speak to other situations, but as the families we share with one another become more nuanced and creative in arrangement, please modify or ignore anything on this list that does not apply to your specific situation.
Lead with authenticity. Your kids can handle hearing that you are a woman who dates! Focus on communicating this in a way they can understand.
As mothers, we do our best to protect our kids from pain, confusion, or a loss of innocence of any kind. Unconsciously, many of us believe this means concealing the part of ourselves that is sexual, wants romance, and is taking steps to experience that in our lives. I adjusted this approach for myself when my oldest daughter asked me where I was going one night and I noticed that it felt inauthentic to mislead her about what was going on. My parenting approach to this and many other things is this: If they are mature enough to ask the question, they are mature enough to understand the answer. They don’t need to hear, “Oh it’s nothing, go back to playing,” or “I’ll tell you when you’re older” or an outright lie. Tell them the truth, but don’t answer more than they are asking. And if you need to share a privacy boundary, that’s okay too! My youngest daughter asked me what a date was and I put it in terms she could understand. “It’s sort of like a play date you have with your friends, but it’s just mommy and a man who I like being around.” My older daughter, in first grade, has seen her friends begin to “couple up” and have crushes, and I shared with her that I had a “crush” when she asked. Our kids need to see us living as whole adults, not compartmentalized versions of ourselves. If they ask and we don’t let them see the many parts of who we are, even in small bits, they won’t know how to accept these many things in themselves too.
Avoid putting in a lot of work to make a first date happen. You have a lot of responsibility on your plate, and there’s no reason to add to that for someone you don’t know.
Schedule time in for a coffee or casual meetup during the day, at a time your kids are not normally with you. Don’t be afraid to schedule a meetup for several days out if needed. There’s a built-in boundary here that can really help filter out the guys who aren’t serious. I typically am not available for several days or a week or even longer to meetup with someone because my schedule stays jam-packed. It says a lot about a man when he stays in touch that long and keeps our plans. The man who wants to be with you has got this and he’s going to stay on top of it! You don’t have to go to long lengths to make yourself available or get dressed up. It’s perfectly fine to show up to coffee in those yoga pants you feel great in, or the jeans and a blouse you wore last week at school pickup. If a touch of lipstick and a swipe of mascara make you feel more yourself, go for it! Casual is key. You want to ask what their relationship goals are and share yours as well!
Pick one night of the week that is yours to go on dates or have a fun night out without kids.
In the past I’ve done this on a night my kids were with their dad, or I’ve had a standing night with a babysitter who came over one evening a week for four hours. This gave me a night off from doing the dinner and bedtime routine, gave me space to take my time getting ready after she arrived, and still left me enough space to make it to a dinner reservation by 7:30pm. For that first post-coffee date, schedule it in on a night you typically have space. My night for dates used to be Tuesdays. I love a weekday because these dates will naturally end after a couple of hours, I can still be in bed on time and ready for school pickup the next day, and I get the chance to receive from a great guy all evening. It’s truly an awesome mid-week pickmeup. I don’t hire babysitters for that first post-coffee date. This is another one that men usually have to wait a bit for with me. I know it works for me and I’m worth it so this is what I’ve stuck to. If you don’t have a date planned for this night, use it for anything else that feels fun to you like a night with a friend, seeing a show, a massage, or a quiet evening with a book. It’s up to you!
Stick to dating people who like to plan.
You are juggling schedules for yourself, your kid(s) and your job. It’s a lot for you to take time out of your day to meet up with a person, so do it with someone who stays on top of the details. They will suggest a time and place, ask what works for you, confirm plans, and make a reservation when you have dinner. Someone who coordinates plans the day of, or who likes to figure things out as they go, likely won’t feel relaxing for you and may even be flakey and stressful.
For the third date and beyond…
Feel free to see your date on one of those precious weekend nights when your kids are with their dad, or hire a babysitter especially for this night. At this point, you’ve established that you like to spend time with this person, and you’ve been able to count on them showing up for the last two dates. It might feel good at this point to give them real space in your calendar, do a non-restaurant fun activity together, and even spend longer than a couple of hours on this date. Take this time to ask thoughtful questions about their dreams, their childhood, their kids if they have them, and don’t be afraid to get silly together.
Set aside time to be with yourself on a regular basis.
It could be an evening every week, an hour every morning, or a special lunch date you take yourself to on Thursdays. Whatever it is, schedule it in and show up for that time with yourself. Having space that’s dedicated to you alone, where nothing needs to be done for anyone else, will help you stay connected to how you’re truly doing and what’s working or not. Give yourself the attention you crave and don’t schedule in kids, work, or dates. This is all about protecting the space you need to feel connected with yourself. Create a self-care ecosystem that can hold you and consider what that includes: possibly therapy, a regular yoga class, time to read or prepare food, a journaling practice, etc.
Make more space for this person for the fourth date and beyond.
By the time you get to the fourth date, you should feel totally confident in this person’s consistent communication, your mutual interest in each other, their ability to have thoughtful conversation, and whether your relationship goals are in alignment. After the fourth date or anytime that you feel ready, you may want to spend the night together, have sex, or want more space to be together. As a mom looking for a serious partner, this was generally the earliest point at which I felt comfortable taking these steps. It is also the point at which I ended a connection if I wasn’t feeling excited and in alignment. Find “that point” for yourself. What level of trust or confidence in a connection do you need in order to open up in more deeply intimate and vulnerable ways? Whatever that answer is, let it guide you.
Have sex without shame.
You might be a mom looking for something more casual as I once was, or you may be just trying to explore yourself and develop dating skills you haven’t had a chance to practice yet. You might be looking for a serious relationship, or a marriage and more children. Regardless of where you are, you deserve to conduct yourself in your sex life with the same permission and acceptance as any single woman without kids, or any married mother for whom there is a greater active conversation about sex and intimacy. Single moms consistently share with me the pressure to keep their sex lives shrouded in secrecy as though they do not even occur, and this societal stigma dates back to the shame women wore for bearing children out of wedlock just decades ago. This is the year 2023 and you have no space in your life for that energy. Be discerning in your sex life in a way that works for you, but you do not need to be guided by shame.
When it’s time for your kids to be aware of who this person is, start a conversation with them well in advance of them meeting your new beau.
You can let them know there’s someone special in your life, and let them ask questions. Spend a period of time connecting with them about the idea of this person. You might FaceTime your man openly and allow them to be curious or say hello. Invite him to send along a small gift for the kids, like candy or chocolate. My man would always fix things at our house and the kids would notice when they came home from their dad’s. When it’s time for them to meet him, keep things casual. Ask your kids what they’d like to do, or see if they want to invite him along to something you all will already be doing. It can be a very short visit at first. Baby steps for the win. There’s no rush.
Last but not least… the most effective way to attract and choose a man who is NOT ready for a relationship with you is to minimize the fact that you’re a mom.
Minimize what you want and need. Minimize what your goals are and the type of conversations you’re willing to have. Show up to your dating life with a clear vision of what you’re looking for and don’t be afraid to share that in an up front and honest way. Look for men who can do the same. This is the fastest way to meet someone who is ready for what you are.
The most important work any of us will do in our dating lives is create boundaries and practices that help us trust ourselves and connect with the other people we meet along our dating journey. You have the creativity, wisdom, and intuition to do that. Where my women struggle to find what they are looking for in their romantic relationships, I offer full-service coaching and custom guidance to help you find the path that makes you feel like your most confident, beautiful, worthy self. Click here to tell me a bit about your needs and goals, and learn more about my coaching availability.