3 Best Tips to Prep for Single Parent Dating!

By Tina Jesso

Where and how to get started in the dating game after a breakup? Dating has changed since you were single, and so have you.  When I was going through my own breakup and divorce and started building a new life for myself with my son, I asked myself – how can I make dating work, when and how to I tell my son there is someone else; and: and am I even ready? Let me help you to navigate the mindset of getting ready for the single-parent dating scene.

  1. Knowing if you are ready.

Everyone is different. Maybe you had checked out of the marriage years before the breakup or maybe it caught you by surprise. In my case, I needed time to heal from a very emotionally dysfunctional relationship. Whatever your situation, keep in mind two things.  First, forgiveness and compassion towards yourself will go a long way to healing and moving on – with your heart intact. This includes taking the time to dig deep – and take responsibility for your part in the breakup, which can be surprisingly the most empowering part of the process.  For most of us, this is really hard to do because it is such an emotionally charged area. Working with a great therapist or coach would help to identify the blind spots! And, now is the perfect time to get reacquainted with you – and really define who you are right now, your values, and work on the silhouette of the type of family you’re hoping to create going forward.

The second thing is – your children need you, all of you. Redefining your smaller family unit with new routines, special new rituals and lots of quality and communication time is key to your children’s emotional stability.  Getting settled in your own routine and rhythm before bringing someone new in your life will go a long way towards creating a solid foundation for your family.

In my case and this is not a rule, I took close to a year to start dating again – just followed my own instinct and what felt right.


  1. Setting up your support system.

Whether you have shared or full custody, developing a support system is crucial – so when you are ready to date, you have trusted caregivers that the kids know and are comfortable with.  As I did not have family in the city where I lived, I also took on the idea “it takes a village”, found a great babysitter and quickly developed some new friendships with other single moms (from school and in the neighborhood). We would either enjoy playdates together or sometimes take care of each other’s children or arrange sleepovers.

And, your support system should include some really good friends and having a few who are also single parents to bounce things off when you are ready to date. That sounding board was really helpful when I jumped back into dating. And, if you don’t have single parent friends – check out a local Meetup Group or even reach out to other parents at your children’s school.


  1. Pre-dating Strategies

Giving some thought to these areas can really prepare you for what is to come and help avoid any unintended consequences with your children.

  • It is probably a good idea not to tell your child that you are dating right away – as it may make them anxious, and they may still be somewhat unsettled since the divorce. My thought was there is really nothing to tell until I am serious about someone.
  • Be ready to move on if you are not feeling it. No need for guilt. You were married before, have children, so there is no rush to create a family.  This is very empowering – as you want to make this a choice because it is right, not because you need a partner. Trust your gut – if it doesn’t feel right don’t question it – just move on. Sometimes the fastest way to a great relationship is knowing what to say no to,
  • If you fall in love, don’t abandon your kids by spending all of your free time with your new love. They still need the routines and the sense of safety and security that you are there for them.
  • How soon should we have “sleepovers”? This was big no no for me when my son was in the house. Try to use your imagination and maybe sleepovers only when the kids are with your ex.
  • How to introduce your kids to the new person in your life? Assuming you truly feel the relationship is serious and has legs, you could start with a casual short introduction or a group activity your kids enjoy. I opted for a 5-minute intro when my new boyfriend came to pick me up for the date. It went well.
  • If you break up – tell your kids in a child friendly way and avoid a detailed account of why you broke up. Your kids deserve an explanation, but shouldn’t be your confidants

With the right strategies, dating can be fun and empowering — just how it’s     meant to feel. You’ve got this!






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