What I Told My Family (and Everyone Else) When I Started Dating an Older Man


After eight years together, Fred and I still don’t have an “official” label for our age gap relationship, and to most people, even our own families, we’re a bit of a mystery.
My 17-year-old and 22-year-old sons have always thought of Fred as mom’s “regular” friend who sleeps in mom’s room because the couch is not comfortable for his old bones. My sister thinks we’re friends with benefits. My parents think we’re a couple and graciously include him in all family gatherings.…

7 Ways to Come Out on Top When Your May-December Relationship Falls Apart


Not every May-December relationship is going to be a match made in heaven, and that’s OK. Besides, part of finding the right partner is dating the wrong ones first. Being on the receiving end of a breakup isn’t easy, but being the one to have to end it isn’t a walk in the park either. If your May-December relationship just isn’t working for you anymore, it’s important that you step up to the plate and do something about it. Be honest with your partner (and yourself), even if that means making the decision to part ways.…

The Worst Time in Your May-December Relationship to Bring Up the Topic of Marriage: Part 1

older man younger woman

On the night of our first date, Brandon, my new older man, had asked to be in an exclusive, long-term relationship. Since I was only 20 years old, I was not sure how to take it all in. There was a big 26-year age difference between Brandon and I and, as anyone else would conclude, I was still a little young to be thinking of marriage. Not that Brandon ever pushed the idea. In fact, he himself once mentioned that marriage was a death trap, to which I laughed. A younger Lena would’ve given Brandon a glare for the comment, but as I got older, I came to realize that marriage was not really everything it was hyped up to be.…

The Day I Introduced My Older Man to My Kids (But Not the Way You’d Think)


I introduced Fred to my sons a couple of months into our age gap relationship. I explained to them that we had tried dating, but since there was such a big age difference—he was 25 years older than me—it just didn’t feel right, so we remained “friends.”
I soon invited him to family holiday gatherings. He was always popular, friendly, and a perfect gentleman around my family. But they got to know him as “mom’s friend,” as I had a mental block that stopped me from calling him my “boyfriend.” The word just didn’t feel right.…