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A Single Mom’s Perspective on Valentine’s Day and Dating After Divorce

I’m not going to sugarcoat it. Being single on Valentine’s Day can really suck. It can be really, really tough, especially if it is on the heels of a divorce. Here you are, nursing a broken heart, and everywhere you look, you are being reminded of what you lost and feared you might never have again. Dealing with these feelings of loss is always challenging, but when the whole world seems to be celebrating love all around you, it can feel like salt in an open wound.


My first post-divorce Valentine’s Day was a wine and cupcake-fueled sob fest. I went all in,
spending the evening watching romantic comedies where everyone finds their happily ever after and lamenting that I would be alone forever. I somehow thought this would make me feel better. It didn’t.


So the next year, I decided to celebrate a different kind of love, the love I had for my daughter. Who says romantic love is the only kind that deserves celebration? I dove headfirst into making the day all about her, decorating the house with glitter hearts, making cupcakes, cooking her favorite dinner, and making her feel like the most special little girl in the world. That definitely made me feel a little better and took the sting out of an otherwise tough day. Each year after that as February 14 th approached, I would try to fight my feelings of loneliness by focusing on making the day wonderful for my girl. When she was about five or six, I saw this great idea on Facebook where a mom did a countdown to Valentine’s Day by putting a heart saying what she loved about her kiddo on their door every day from February first until the big day. I loved the idea and immediately adopted it and have been doing it every year since. It was a great way to give the holiday and new, more positive focus, and while I knew this wouldn’t work forever, it bought me a few years to heal my heart, make peace with the holiday and figure out what was next in the love department.


I finally started to look at those chocolate hearts and diamond commercials with a glimmer of hope and excitement again. Maybe I wasn’t out of this love game after all. The dust had settled from my divorce, I had found a new normal and I was happy. Maybe it was time to open the door to my heart again. But was I ready? How do you know when you are ready to date again??


First, know that there is no right answer. This is a big decision and getting to the space where
you feel like you are ready may take some time. Be okay with that. Honestly, there is no rule
that you EVER have to date again if you don’t want to, but for most of us, the desire to be in a
healthy, happy partnership does return. If you find yourself thinking about jumping back into
the dating pool, here are a few ways to tell if you really are ready.

  • You took the time to heal. – Divorce is painful, no matter the circumstance, and there will be plenty of emotions to work through to make it to the other side. Make sure that you have taken the time to deal with any anger regarding the loss or anger at your ex- spouse. In order to move on, you have to be emotionally ready and available to let someone in, and you can’t do that if you are still holding on to the pain of your lost relationship. Whether you see a therapist or do your healing on your own, you will know you have reached that place when you are at peace with yourself. You can talk about the relationship without a great deal of emotional reactivity and you have taken the time to understand your feelings. You are confident in who you are, and where you are going and can embrace the divorce as part of your story but not something that defines you.
  • You have done the work on yourself. – Healing from a divorce involves not just dealing with the grief, but also digging into past patterns of behavior that contributed to unhealthy relationships. You have taken responsibility for your part in the divorce and also taken stock of what you have learned from the experience that will help you in future relationships. Make sure you have taken the time to prioritize yourself and your needs and learn to fall in love with yourself again. It’s crucial that you become comfortable in your own skin again and have goals that have nothing to do with being in a relationship. As crazy as it sounds, you know you are ready to date again when you can say you really are okay with being single.
  • You are clear about why you want to date again, and what you want. – It’s important to understand your motivation for joining the dating scene again. It should not be because you are feeling pressured by others to “get back out there” or you think there is some internal clock that is saying you should be ready to move it. Jumping back in too soon can have disastrous effects, so it’s crucial to get clear on why this is important to you now and what need is this going to fill. Be honest with yourself and make sure you are not using dating to run away from uncomfortable feelings or fill the void left by your ex or provide emotional or financial security. Also, be clear on what it is you want from your dating experience. Think about what your needs are, what boundaries you have, and what your deal breakers might be. If your standards and intentions are clear, that is a good indication that you are in a great place to welcome someone into your life.
  • You have opened yourself to new possibilities. – An important first step to getting ready to date again is to discover your new post-divorce social self. Have you worked to expand your social circle, met new people without the pressure of a dating situation, and started to build a fulfilling social love? All of these can help ease you back into life as a single person and help build a full life into which you can then welcome a partner. Make sure you already have fulfilling relationships in your life and feel like you are on firm social footing as an individual. As cute as it sounds, we should not be looking for someone to complete us, rather we should have done the work to be completely ourselves and be open to meeting someone who can add to that.
  • You are prepared for the good and the bad of dating. – The reality of dating is that there will, absolutely, be bad dates. You must be honest about how open you are to roll with the punches and keep putting yourself out there. If one lousy date would turn you off from the whole experience, you may not be ready to test the waters just yet. The hope is that even if you don’t make a love connection, dating will bring some fun and exciting experiences, but there will be some duds along the way. Dating should feel exciting and hopeful, not full of anxiety. Understand that there will be ups and downs, but if you can keep an open mind and a sense of humor, you might find what you are looking for.

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One Comment

  1. Good job. Good words. The journey is long, the pain is real, the growth is measurable. From pebbles, to boulders to mountains of obstacles. Yet looking back memories hide honestly clouding reality tragically. We ALL deserve that 1.

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