Dear Ask Wendy,
I have known this woman for about twenty years. We have many mutual friends, have flirted over the years, and now we are both in a position to steer this friendship into a more intimate relationship. Despite the difference in our respective ages, we have always been tight friends. Sometimes I think we are about there (I admit that I am trying to steer us there). The thing is, do you think that maybe she is being ageist? I am sixty, she forty two, and that makes her the oldest woman I ever dated.
L.K.
Dear L.K.,
Hmmmm.
I wasn’t going to come out and play the advice game this month, given that I’m still hard at work on my Manifesto for the New American Century, but your letter, implying as it does issues close to my heart, gave me pause. Though I am a little confused about what your actual question is here. Is the woman, perhaps, refusing to be steered? Is that what you mean by worrying that she’s ageist? But your follow up comment that, at forty two, she is “the oldest woman I ever dated” seems to give us a clue to what might be holding her up.
Let’s face it, L.K., one of the pleasures of getting older is that a difference of eighteen years barely registers on the radar. It really depends on the experiences of the two parties concerned. I know plenty of forty year olds who are a lot more mature in their outlook than someone in his/her sixties who’s refused to grow up.
And I know what I’m talking about. Peter Pan was about two hundred and ten years old when we first met. I might have been twelve at that point, but I was ages older emotionally. I outgrew him by the time I was sixteen. And that wasn’t ageism either. That was pure exasperation with somebody whose unchanged philosophy of life was: “Think happy thoughts and throw yourself out the window.” After a couple of years of “I can fly, I can fly, I can fly!” and him manipulating me into fights with that horrible Tink, I’d had it. So, recently, has Tiger Lily. And why? Because it doesn’t matter how old the guy is, if he won’t grow up, you’ve got to leave him to the twenty year olds.
So is your problem that you think she’s too old for you? If you think so, it’s probably true, and you should save both of you a lot of hassle and try to date her daughter. But if you’re serious about wanting to take things to the next level, I’d just be honest with her: emphasize the friendship, and the trust that’s grown up over the years, along with your long and rich history together.
After all, you say you’ve known this woman for about twenty years. She’s had plenty of time to assess the situation. Why don’t you just sit her down and give her a frank “how about it?” She’s certainly old enough to make up her own mind. Just make sure you’ve made up yours first. My guess is that’s what’s holding her back, if anything.
Good luck. And let me know how it goes. If there’s one thing Ask Wendy likes, it’s a happy love affair. At whatever age.
Yrs,
Ask Wendy
(want advice from Ask Wendy? even though she's busy working on her MANIFESTO FOR A NEW AMERICAN CENTURY, she's never too busy to butt into your life. email her at askwendy@exterminatingangel.com.)