Dating as a Single Mom: How to Know When You’re Ready

You finally have a Friday evening to yourself. A friend offers to introduce you to someone, and for a minute, you’re excited. Then you start thinking about how tired you’ll be after work, what your kids might think if they found out, and whether you even remember how to be on a first date. By the time you reply, you’re tempted to say you’re busy.

Dating as a single mom can bring up several questions at once. Do I want to meet someone? Do I have time to see them? What if I like them and they want more time than I can give? You might know the answer to one of those questions and feel unsure about the others. It can help to look at each one separately.

When you want to date and feel guilty about it

You might be looking forward to dinner with someone and still hesitate when your child asks why you’re going out. Or you finally have an evening when the kids are with their other parent, and you wonder whether you should use it to catch up on laundry, see a friend, go on a date, or sit on the couch where nobody needs anything from you.

It can help to get specific about the guilt. Are you worried about missing a bedtime your child has been struggling with? That’s a practical concern you can think through. Or do you feel guilty even when your child is happily spending the evening with someone they trust? You might be so used to organizing your time around other people that choosing something for yourself feels uncomfortable, even when everyone is taken care of.

Wanting a partner, missing physical affection, or looking forward to a conversation that has nothing to do with school pickup are all understandable. You can also decide that what you want most this Friday is an early night. You get to make that decision again next week.

How do you know if you’re ready to date again?

You can still miss a former partner, feel nervous before a first date, or be figuring out what you want. Maybe you’ve been parenting on your own for years and have never tried dating with kids at home. Maybe you’re dating after divorce, a breakup, or the death of a partner. In each case, it can help to ask what dating would be like for you right now, with the time and emotional energy you have.

You’re curious about the person in front of you

You might notice that someone laughs like your former partner or that a question about your weekend brings back a memory. Pay attention to what happens next. Can you stay interested in this person and learn something about them? Or do you spend most of the evening thinking about the relationship that ended and wishing you were with your former partner?

If that happens on one date, it may tell you more about that evening than about your readiness. If it happens every time you try to meet someone, or you find that a date leaves you feeling raw for days, you might want to give yourself more time or talk with someone about what’s coming up.

You can say what works for you, even if it feels awkward

Maybe you can only meet every other Saturday. Maybe a late dinner will make the next morning miserable. Or maybe you like someone and still want to wait before planning a weekend together. You can start with a sentence you’d actually say. “I’d like to see you again. This week is full for me, but I’m free next Saturday.”

Notice what happens for you after you say it. Do you feel an urge to take it back or offer a time you know won’t work? It can be helpful to get curious about what you imagine will happen if you let your answer stand. You might be used to someone taking your limits personally, so even an ordinary scheduling conversation can feel like a bigger risk than it appears.

How you respond when a date doesn’t work out

Say you have a good time, expect to hear from the person, and then hear nothing. Of course you might feel let down. If that disappointment quickly turns into Nobody wants to date someone with kids or I must have said something wrong, notice how far you’ve gone from what you actually know about the date.

You might find it helpful to talk with a friend who can hear how disappointed you are and help you remember the rest of the evening. Maybe you were doing most of the work to keep the conversation going. Maybe you genuinely enjoyed yourself and wish it had gone somewhere. Either way, you have a little more information about what you liked and what you want to pay attention to next time.

How to make time for dating as a busy single mom

Start with the time you actually have. If you have ninety minutes between work and pickup and there’s a café nearby, that might work better than trying to find a sitter for dinner. If coordinating childcare would make a first date feel like a big commitment, you might prefer a short phone call first. Some weeks you may have no time or interest in dating at all.

You can be upfront about your availability without explaining every detail of your family’s schedule. “I usually plan a few days ahead” may be enough. If your child gets sick and you need to reschedule, you can say you’d like to find another time. How someone responds can tell you something about what it’s like to make plans with them when real life gets in the way.

Someone might reasonably want to see you more often than you’re available. You may even want that too. If you keep saying yes to plans that leave you scrambling, it’s worth asking what pace would let you look forward to seeing the person. You can learn a lot about someone by seeing how the two of you handle an ordinary difference like that.

What past relationships can bring up when you start dating

You might go out with someone who follows through on plans and feel strangely underwhelmed. Or you might find yourself drawn to someone who’s affectionate in person but hard to reach between dates. If you’ve spent years trying to figure out where you stand with someone, you may be used to putting a lot of thought and effort into keeping their interest. When a new person is inconsistent, you can find yourself doing that again before you’ve even decided how much you like them.

You can start by looking at a specific moment. You sent a text yesterday and they haven’t answered. What did you tell yourself when you noticed? Did you feel hurt, get busy doing something else, or send a second message even though you wanted to wait? Has this person generally been reliable, or have you already been left waiting several times? The answers can help you understand both what the situation brings up for you and what you’re learning about this person.

In my attachment-based therapy practice in Encino, we can look at moments like these and talk about what you learned to expect from people you care about. That might mean understanding why you apologize before asking for something or why you find it hard to trust someone who seems genuinely interested. If you’re trying to make sense of a new person’s behavior, I also wrote about dating red flags and what to watch for early on.

When to tell your kids you’re dating

Going on a date and introducing someone to your children are two separate decisions. You can take time to get to know someone before bringing them into your children’s lives. If your child asks why you’re going out, how much you share can depend on their age, what they’re asking, and what’s actually happening. A younger child might mainly want to know who’s putting them to bed. A teenager may already have figured out that you’re dating and want you to say it plainly.

If a relationship becomes more established and you’re considering an introduction, think about how the person has handled your limits and how your child has been doing with changes at home. You could start with a short, low-pressure meeting and talk with your child afterward. If they don’t have much to say right away, you can check in later.

What if your child is upset about you dating?

Try asking what they imagine will change. They might be afraid that Saturday mornings together will disappear. They might wonder whether it’s okay to like someone new when they miss their other parent. If they’re worried about losing a routine they count on, you can tell them what will stay the same and follow through. If they’re sad or angry, you can hear them out before trying to explain why you’re dating.

It can be hard to hear your child say they wish you’d stop seeing someone, especially if you’re already worried about how your decisions affect them. In individual therapy for parents in Encino, we can talk through what their reaction brings up for you and how you want to respond. Those sessions are for you as the parent.

Individual dating and relationship therapy in Encino and online in California

Maybe you want to date but freeze when someone asks to see you again. Maybe you’ve been seeing someone and find yourself agreeing to things you later wish you’d spoken up about. Or maybe you’re still deciding whether you have the time and interest to meet anyone right now. Any of those is a place we can start.

I offer dating and relationship therapy in Encino and online throughout California. We can talk about what dating brings up for you, how past relationships might be affecting what you expect now, and what you want a relationship to look like alongside the life you have with your kids.

If you’d like to get a sense of how I work and see whether we might be a good fit, you’re welcome to schedule a free 30-minute phone consultation.