And I've added a couple of my own tips for good measure, since I am the younger woman and all.
But I've been watching and compiled a list of DOs and DON' Ts from Jess's experience dating the sophisticated Dermot Mulroney as Fancypants, who's a whopping twelve years older.
There are actually two things to consider here – his children, and your potential children. As a man gets older, it becomes increasingly likely that he will have fathered some children along the way.
These children will take up his time, whether they live with him or he spends his weekends with them.
Russell confesses he hasn't dated since 1989 and Jess replies, "That was the year I learned to use the toaster by myself." Not so hot.
DO be lovey dovey, but DON' T nickname him something based on his age (Fancypants is cool, though).
Now, I’m not saying these are conscious reasons why dating a man quite a bit older—there have been several moments when I’ve thought that going out with someone closer to my age would be much simpler.
I even tried it when my boyfriend and I took a short break, and I found it was painstakingly difficult and more complicated than my experience dating an older guy. The texting games (How long should I wait to text him back? It’s exhausting), the fear of commitment that plagues most twentysomethings, and the simple fact that most guys my age aren’t as emotionally mature as I am.
Beyond the obvious differences, what is there under the surface that you need to know?
You never know when you’ll find love – it often comes from the most surprising places.
And at e Harmony, as we’re focused on deep-down compatibility, who you connect with can be even more surprising.
Most importantly talk everything through; these aren’t issues that are just going to go away.
Meeting someone later in life means they’re more likely to have become set in their ways.
Anyone who’s been in a serious long-term relationship knows the journey isn’t without certain challenges, and when you’re dating an older man—we’re talking a decade or more—things can get even trickier.