After instances such as divorce, the death of a spouse, or simply after being single for a long time, it can be harrowing to dive back into the dating pool. Read the stories and advice from our contributors.

Single parent dating:

In some ways, it’s a lot harder dating as a parent because you have to match someone to all of you, not just yourself.  I was a single parent for 10 years. Because my kids were small, I was looking not only for a partner for myself, but for someone who would be a good stepfather. Introducing a partner to your children is tricky. Because my boys have a great dad who had them almost half the time, I could date for several months before introducing a boyfriend to my children. Some boyfriends were obviously just for me and never introduced to my kids. One man I dated was a serious candidate for a potential partner. We spent time together as a family for almost a year. Things didn’t work out between us, which was a bit difficult for my children to understand.

After 10 years of dating, I did find a wonderful man who I love and the boys adore and respect, and who is committed to being a good stepfather. He has two girls and I am learning to be a stepmother as well. Fortunately, we have the same parenting schedules, so have alone time together.

Valentine’s as a single person:

When I was younger, I would be so disappointed when I did not get the box of heart chocolates and the pink roses I so desperately desired (but had utterly failed to communicate to my husband). And then I would get angry. After I got divorced, I spoiled myself rotten on Valentine’s. I bought the best chocolates, my favourite flowers, got sweet, lovely cards from my children, and watched chick flicks on Netflix. I rather enjoyed Valentine’s Day when I was single because it met all my expectations.

Getting what you want:

As I got older, I learned more about my love languages. Receiving gifts is one. For me it’s less about receiving a gift as it is having someone thinking to buy a gift and spending the time and effort to do it. Now that I have a partner again, we have a shared Excel spreadsheet and I have lists of things I love to receive and I have communicated (clearly and unequivocally) that I love to receive gifts. He can surprise me with anything, but if that is too much pressure, he can find something on the list and I am happy.

Rebecca Lippiatt

Dating when fiercely independent:

Not yet a senior, yet looking like one, I have tried dating off and on (more off than on) since 2010. This past summer, my ears perked up, kicking me into action when a fellow volunteer revealed he had never married. Reluctant to lose his independence, he also wanted to avoid being tied down.

After turning my flirt back on, his independence disappeared into neediness. Sigh.

If someone matched my fierce independence, valued long periods of time on their own, and matched me in the extreme planning department, arranging semi-regular rendezvous may work out for trips, dancing, fun, and games. I know any tendency to flirt is guided by a high alert to avoid any cling-ons and types desiring 24-7 exclusiveness.

Rusti Lehay

Featured Image: Dating can be complicated when you’re a single parent. | Pixabay