How to Know When You’re Ready to Date Again

How to Know When You’re Ready to Date Again

When you think about dating, what are you more afraid of? Being lonely or being hurt? This month we're talking about relationships, and today we're going to talk about how to know when you're ready to date. Dating is a big topic. So, ladies, one of you -  

What is some advice that you got about dating after divorce?

Some great advice I got was to have fun. I was approaching it with so much seriousness and weight and over-analyzing, and I needed to lighten up a little bit and realize that dating isn't the same as diving into a long-term relationship. It's just dating.

One of the questions we get most often is, how will I know when I'm ready to date again? We've heard advice on both ends of the spectrum. On one side friends tell us, just get out there. And on the other end we hear we need to follow a formula of waiting a year for every year we were married. Added to how we feel about dating and how our kids feel about us dating, which complicates everything even more. So, what do we do?

Today we're going to talk about three main points. Number one, the best question to ask yourself before you start dating again. Number two, what relationships can and cannot do for you. And third, talking to our kids about when we're ready to date.

Knowing when to date again after divorce, or maybe the death of a spouse is tough. There are a lot of factors. First, let's talk about the timing, and then we'll get into the best question to ask yourself before you start dating.

What do you think is the best amount of time to wait? Which factors play into this? And how long did you wait?

I waited two years before I started dating again. What do I think is the best amount of time to wait? It really varies and is super individual. I think giving yourself enough time to deal with the grief and loss of what you've experienced is important. And then beyond that, knowing what you need to do differently next time, however long that takes. For some people it might be two years, like it was for me, for another person, it might be double that or perhaps even longer. The wisdom is in self-awareness and seeking some input from others.

In the two years, I had moved beyond some of the deep pain of the loss I had experienced. I wasn't in turmoil, and I had found some stability in my life. My schedule was pretty consistent. I had an idea of the routine with my kids doing it on my own. There were some things spiritually too—my connection to God was really solid, and I had a good community around me. Friends. I wasn't super lonely or desperate. I felt really healthy and happy after a period of deep pain after divorce.

Do you think there's a formula for how long to wait?

No. It's individual. You have to decide for yourself. Sometimes like me, you have to learn the hard way. A formula puts you in a box or backs you into a corner.

Something that factors into this idea of how long also depends on how you ended the relationship. Because I have talked to single parents that for years prior to the actual end of the marriage, they had begun a journey of self-awareness and healing. You can't say that it starts on divorce day or the day your spouse dies. It does look different for those that have lost people to death. That's a whole other level of exploration. It's safe to say there is no specific amount of time. It really is about your own healing.

This leads us to the question we feel is really paramount to ask yourself when you're thinking about dating again. The most important question to ask yourself is, “Do I feel whole if I never date again?” It’s a really important distinction. I waited approximately five years.

When I started dating again, I had a sense that if I'm single for the rest of my life, I'll be okay. That's why I think this question is really important. It doesn't mean you're perfect. But if you look at the future, if you never dated again, would you still feel whole without dating?

Feeling whole and content in some ways with where I'm at in life and who I am and the kind of person I am and where I'm going, the purposes God has for me is really true for me. I feel really solid in that. But the longing for connection is still very real. And I'm even aware of some of the time trajectories. I'm 50 years old. There is an awareness for me that if I do want another long-term relationship or get married again, there’s a sort of time limit. But really balancing the longing and the timing with trusting God's sovereignty, trusting His direction. I have an amazing full rich life right now with or without someone. I would like to add someone or be included in someone else's life. That's still true. And so for me, there's a both/and that I can't get away from.

Scripture does say it's not good for man to be alone. It starts in Genesis. You will not be able to bring to a relationship what you need to bring if you haven't done your work.

The other thing is, I have learned so much from being in a relationship and healed so much from being in a relationship that I don't know that I would've gotten that otherwise. I feel like I am more whole now because of my relationship. If something were to happen today, I know for a fact that I would be okay and that I would still feel whole.

Knowing that you're in a good place to date is being aware that you are still on a learning curve. You don't have it all figured out. You need guidance, you need input, and you need safe people to add some wisdom and direction. There's an appropriate caution even if you feel really ready.

Our second point is what relationships do or don't do. It's safe to say that there is no best answer to when you start dating again. But there are some specific questions you can ask yourself regarding self-awareness, about feeling whole, which doesn't mean there's no desire. It means you have put to rest some of the things that you’ve been carrying around and the expectations that you put on dating. One of the most important things about relationships is that we work things out in relationship.

What is a misconception about the purpose of relationships?  

The belief that a new relationship or that your next relationship will make you better. Also, that you have to have a relationship in order to make you whole. There can definitely be some healing in a new relationship, but it shouldn’t be the reason why you get into a relationship. I believe God can show you things that need healing that could only happen in a relationship. For example, if you struggle with feeling unworthy, unloved, or unlovable a healthy relationship can help heal some of those lies. You need to have a solid sense of who you are in Christ, a solid sense of what your values are and be able to stand on your own two feet before you start a new relationship.

This topic is so nuanced and specific. If someone's coming out of an abusive situation, there's a lot of trust that needs to be rebuilt. There are all kinds of nuances to this, but it does start with self-awareness. Relationships are not meant to complete us. They're supposed to enhance our lives and bring out the best versions of ourselves.

It's also important to recognize it's going to look different for those who’ve lost a spouse to death. You might have a sense of guilt if you've lost someone to death. Statistically it takes widows and widowers much longer to move on because they're not only mourning the loss, but there can be feelings of betrayal. It's complex. It's not one size fits all.

After a divorce there can be a sadness of starting over and the sadness of moving on—there’s a finality to it, that there is no chance of reconciling. The sadness is an important part of the process.

Dating and moving on can bring on more feelings of grief. And there's also the fear that comes along with trusting yourself again to make the right decision. Because the thing that I told myself for a long time was that my picker was broken because I was seeing all these patterns in my relationships. I can't trust me to make this decision.

One helpful way to think about dating is that what got us here won't get us there, which means we have to start recognizing that we need to start looking at some things differently. For instance, I am married to someone that I never would've picked out in my past life. I wasn't looking for someone just like me anymore. We do have patterns and we have made decisions in our past that have not resulted in great things, whether of our doing or the other person's doing. There are scars. We need to be willing to kind of flex in that area.

It’s important to say that you need to give relationships time before you make a final commitment, a lot of time. I dated for three and a half years before I got married and I'm not saying that that's the right amount of time, but so much healing happens in relationships as you give it time. And not only is length of time important to understand and grow, but pace can really be important too. Not diving in too quickly, not taking it to the next level in a millisecond. Really recognizing that before diving deep relationally having the wisdom and the self-control and the wherewithal within yourself to think about your need to assess, the need to take things slow.  

This is when fear can actually help us. If you’re not ready to trust, then don’t trust right now. Take your time because the main point here is that relationships don't fix our problems, we can be fixed in the midst of relationship but only if we're willing to do our own work.

How and when and where do we start involving our kids in this idea that we're going to start dating again?

Our kids are all different and will have different feelings. Some solo parents I’ve talked to said their kids encouraged them to date again, but then when they start dating, the kids changed their mind and don't want the parent to date. And there’s everything in between.

If your kids are really young, they may not even be aware that you’ve started dating again. One strategy, if you have 50-50 custody is to limit date nights to when your kids are with the other parent.

It’s complex and does depend on the age of your kids. Their maturity and their awareness and whatever else is going on in their lives. When I first started dating, my kids weren't ready, and I really felt ready. And I thought that my readiness would be enough to help them be ready but that was not the case, so it was very painful and difficult. My kid’s resistance to me dating (they were 12 and 15 at the time) really played a strong role in the stress on the relationship that I was developing. My kids were very territorial. I was their primary custodial parent. Their dad was not in the picture, which makes a big difference. Their sense of abandonment and their fear of losing me, having already felt distant from their other parent, was a huge issue for us. And so, assessing your kid's readiness is vital. I didn't give it the weight that it needed.

If I had it to do over again, I would try to approach it a little bit differently. The first time that my kids met this person that I dated for a long time I would've prepped them more. I would've talked them through it more. I sort of sprung it on them. I did talk to them, but they needed more, and I didn't recognize that. I thought I could approach it more casually and in hindsight, they needed a lot more preparation. I would go back and take more time to intentionally talk with them, hear their fears and their hurts instead of assuming that because I was okay and in a strong place, that they would be okay.

Making sure that you're allowing your kids to have a voice into it.  And a voice is different than a vote. I never talked about the idea that I would date again with my kids, and I regret this. I felt in some way that dating would create some instability. I didn’t let them into my decision to date. The result of this was later when I got engaged, it was very much at the protest of my girls. In fact, at my wedding, they were so against it that my oldest wouldn't even wear shoes. She was just barefoot. We got married at my house in a private ceremony with some friends.  I remember telling them when I decided to get engaged, you don't have to like this person. She doesn’t replace your mom. I'm asking you to trust me that this is the best for our family.

The kids see dating as a disruption. Their world has already been rocked by either death or divorce. Then you build this cadence of how life is as a solo parent. So, when you introduce dating, be prepared for disruption. It doesn't mean it's the wrong person, it doesn't mean it's the right person.

Now my girls are really close to my wife. Just remember, how the kids feel initially even if it's in protest of you dating isn’t necessarily where it's going to end up because we have to see dating as a disruption. Don’t minimize how much of a disruption it is. Give your kids a voice, not a vote.

If you're taking your time and you're giving them a voice, you can trust your judgment. We have to be adults. We cannot be codependent with our kids and let them make the decisions for our lives.


The most important thing we can ask ourselves when we're thinking about dating again is - are we whole and will I be whole?

A new relationship can't fix you or your problems. You can heal in the midst of relationship, but it’s not a Jerry Maguire “you complete me” thing ever.

If you're taking your time and you're giving your kids a voice, you can trust your judgment and make a decision on what's best for you.

Listener Question

Hi, this is Sharon. I'm a single mom. What's one thing you have sacrificed for your kids because you're a single parent that is unseen that no one not even your kids know about?

One big sacrifice is not getting married or moving to the next level in my relationship because it would be a big disruption to my son. We’d have to move and I’m not willing to disrupt his community—and my community, the relationships we’ve built. I willingly sacrifice it because it’s important to me.

Another example is staying in the house that they grew up in. Their dad and I leave one week at a time. They don't recognize how difficult that's been on each of us. They know that we're doing it for their good, but man, that's tough. My heart goes out to single parent kids. You have to pack up and move once a week. I know what that's like, and kids are resilient and strong.

The sacrifice that I felt that my kids don't know about is I had full custody all the time. So, I never had time off. I loved being with my girls, but I would've loved to have a social life. I would've loved to have a week or a weekend when I didn't have them so that I could be with other people. It was a sacrifice, but it was one that I gladly did.

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