Category: May-December romance


November 18th, 2010 — 3:19pm

Not too long ago, I blogged about my first experience of dating a much younger guy, J. This week, I rediscovered why the May-December dynamic tends to work better when it’s the other way around.

Mr. 21-year-old had returned from a last-minute trip to London eager to see me. It had been a couple of weeks, so I happily accepted his invitation to get together in Roosevelt Island. Especially since I received this text from him before he took off:

“I wana see u so close that my vision blurs, I wanna hold u so tight that I can feel ur heart beat, wana kiss u for as long as I can hold my breath.”

Typos notwithstanding, who wouldn’t enjoy being the object of such ardor?

City Splendor: my third date with J was all about Roosevelt Island’s view of NYC’s skyline

So I head out to Roosevelt Island. J takes me to a pier with sweeping city views. We kiss and I savor the moment, wondering what else J has in store. I find out soon enough when he drives me to a second scenic overlook. Much as I love taking in NYC’s breathtaking skyline from various vantage points, I was getting hungry at this point and craving more than endless smooching.

We get back in J’s car, where he proceeds to blare some ghetto fabulous music (the kind that those parental advisory stickers were made for) as we drive to Jackson Heights for takeout. With more four letter lyrics than I’ve heard since my college days, I found myself thinking I’m way too old for this.

That reality hit home even more when J followed up the next day with a text message that said–

“I wana suck on ur nip****s n then I want u to suck me off.”

Now I know why I’m not a fan of sexting, or spending time with a guy whose idea of fun is driving from one makeout spot to another.

To be fair, I suppose, J is only 21, the perfect time for being wild and carefree. Though I have my wild and carefree side too, I now know I would rather indulge it with someone who’s had more life experience. Someone closer to my own age, say, 25 and up.

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November 6th, 2010 — 5:14pm

Not too long ago, I about going out with twentysomething bachelor Jay. It was another kind of age difference during my subsequent date with business exec/actor Jeff, 47.

When it comes to May-December romance, I’ve always preferred being the younger one. Older men tend to know what they want and not waste time playing games. Over drinks with Jeff at cozy wine bar Riposo 72, he showed me how engaging it is to be around someone who is truly comfortable in his own skin — the kind of confidence that only comes with years of life experience.

We talked about our mutual affinity for family bonding and European travel — and about the high standards we have for happily ever after because of the examples set by our respective parents. Jeff spoke candidly about not wanting to settle, and I found myself appreciating the subject, something that’s (understandably) off limits with Jay because he’s so young. Younger, in fact, than he first led me to believe.

Just before date number two, Jay admitted that he’s not really 25, he’s 21. I was floored. Partly because he exudes more maturity than his thirtysomething peers, mostly because, well, I think that officially makes me a cougar. How can I spend time with a guy who’s just graduated from college when I’m in the second half of my thirties?

But then, I think about my first two boyfriends. They were 16 years older and I was Jay’s age when I dated them. I would’ve missed out on two great, life changing experiences had they dismissed me because of my age. It’s what connects two people that matters, not the years between them — as both Jeff and Jay have reminded me.

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October 27th, 2010 — 4:30pm

Actress Billie Burke once said age is something that doesn’t matter unless you’re a cheese. Two recent dates reminded me how true this is when it comes to romance.

I’ve always been pretty liberal-minded when it comes to May-December romances — an inevitable consequence of being raised by parents with a 25-year spread (Dad was older). Which is why I was intrigued to be on the receiving end of twentysomething bachelor Jay’s attentions.

TGI Friday’s: Jay and I met here. Don’t laugh.

We met at TGI Friday’s. Though this isn’t a usual hotspot for me, there’s something to be said for cheap happy hour specials in an unpretentious setting.

Jay and I fell into easy conversation, talking about life and work. He admitted to feeling increasing pressure on the job to be an “a–hole,” and I couldn’t help thinking how that could also apply to after work behavior in the Big Apple. He spoke with a refreshing candor, and proceeded to call me the next day so we could make plans.

Over a delicious dinner at the South Street Seaport, I thanked Jay for getting in touch right away.

“Why wouldn’t I?” he asked with genuine curiosity.

“You’ll find the longer you’re single in New York, the more deliberation and waiting there seems to be about when to follow up after meeting someone,” I said, feeling how jaded I sounded.

“That seems like a waste of time and energy,” he said.

Time and experience have yet to temper Jay’s directness, as he proved again when he admitted he’s not looking for anything serious. I appreciated his honesty, especially since it’s a far cry from the noncommittal thirty something bachelors populating New York’s dating scene.

Case in point — an old flame of mine from last summer. Said old flame has been in touch several times over the last year. When I finally agreed to meet him for coffee, he downplayed it, saying–

“I would hardly call sending a few emails persistence.”

Of course he wouldn’t.

He proceeds to say that he wants to cook for me, and mentions a few restaurants he would like to take me to. We make a dinner date. He cancels it, proving why there’s something to be said for avoiding NYC men in their thirties. Serious or not, their decidedly younger and older peers seem to have a much better handle on what they want — and how to articulate it.

Coming up…a memorable date with a bachelor at the other end of the spectrum!

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October 17th, 2009 — 3:20pm

Last weekend, my friend Bobbi and I enjoyed a girls night out in NYC’s Meatpacking District.

Agave: adobe walls and flickering candles contribute to the hip yet relaxed atmosphere at this Mexican eatery

Over dinner and a shared pitcher of sangria at lively Mexican eatery Agave, we talked about past and present affairs of the heart — from our respective experiences of cops being major players to our different takes on May-December romance.

Bobbi is having fun with a twentysomething personal trainer-aspiring rapper. I prefer men who are my contemporaries or older, having had three boyfriends who were approximately 15 years my senior, and parents with a 25- year spread between them.

Later, Bobbi and I encountered a well-coiffed mixture of twenty and thirtysomethings at a crowded bar across from Pastis. Just when we were about to call it a night after a few glasses of wine, a tall, adorable guy with an Australian accent brushed past us with a group of male friends.

Originally from Melbourne, he introduced himself as Dave and quickly reminded me why Aussies have a reputation for being great storytellers.

Dave told us the tale of how he met his most recent girlfriend. While traveling to Africa, he found himself naked when his clothes were stolen during an afternoon of skinny dipping. His soon-to-be sweetheart stumbled upon him and took pity on his embarrassing situation, and so a romance was born.

Which just proves that you never really know when Cupid is going to strike. And that it’s preferable to be fully clothed when he does.

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September 18th, 2009 — 12:38am

Thursday, after my action-packed experience at Fashion Week, I met up for dinner with my old flame Alain.

Like many blasts from the past these days, this one came about through Facebook. Now married and living in Helsinki, Alain reached out and I was excited to hear from him. Fifteen years my senior, he was my first experience of May-December romance back in the day.

It had been well over a decade since we’d last seen each other, so we had lots to talk about over dinner at Accademia di Vino.

Accademia di Vino: Alain and I talked about life, love and tennis over dinner at this UES hotspot

We talked about timing and the role it plays in finding happily ever after. Alain said it was when he decided he was going to take a break from the New York dating scene that the tide turned. Alain started hearing from several old girlfriends, but it was on the tennis court where he met his match.

Months later, when his Finnish-born sweetheart proposed by declaring they were getting married in her hometown, he was more than happy to say yes. As he shared this, I couldn’t help thinking that, when you find your life’s partner, the semantics of how you wind up together don’t seem to matter so much.

As he did many so years ago, Alain demonstrated that he’s one of the good guys.

“I couldn’t leave this earth,” he told me, “without telling you how sweet you are.”

Wow.

Coming up…a new author’s delectable approach to dating and a look at how to break up without being mean.

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September 17th, 2009 — 7:38pm

Thursday, after my action-packed experience at Fashion Week, I met up for dinner with my old flame Alain.

Like many blasts from the past these days, this one came about through Facebook. Now married and living in Helsinki, Alain reached out and I was excited to hear from him. Fifteen years my senior, he was my first experience of May-December romance back in the day.

It had been well over a decade since we’d last seen each other, so we had lots to talk about over dinner at Accademia di Vino.

Accademia di Vino: Alain and I talked about life, love and tennis over dinner at this UES hotspot

We talked about timing and the role it plays in finding happily ever after. Alain said it was when he decided he was going to take a break from the New York dating scene that the tide turned. Alain started hearing from several old girlfriends, but it was on the tennis court where he met his match.

Months later, when his Finnish-born sweetheart proposed by declaring they were getting married in her hometown, he was more than happy to say yes. As he shared this, I couldn’t help thinking that, when you find your life’s partner, the semantics of how you wind up together don’t seem to matter so much.

As he did many so years ago, Alain demonstrated that he’s one of the good guys.

“I couldn’t leave this earth,” he told me, “without telling you how sweet you are.”

Wow.

Coming up…a new author’s delectable approach to dating and a look at how to break up without being mean.

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September 4th, 2009 — 8:00pm

Breaking up is hard to do, especially when it’s with someone who’s treated you like a princess. Back in ‘97, my second and final split from then-boyfriend Larry had me guilt ridden over hurting such a great guy.

A 16-year age difference proved to be too much for us to overcome, as I realized I wasn’t ready to settle down. Still, after a year together and one brief trial split, saying goodbye wasn’t easy.

I now Open The Vault and take you back to January of 1997…
January 28th, 1997
New York, NY

Dear Diary,

Larry and I broke up again the other night — and this time I think it’s for good.

Unlike our previous split (I initiated both), this separation was not the result of an impulse to retaliate for anything. When I ended things back in October, it was primarily because he had let me down when I needed him most.

Ironically, more so than he ever did before — and that’s saying a lot — Larry treated me like a princess these last couple of months. Casting off internal demons that had kept him somewhat closed off, he revealed a tender, romantic streak the likes of which I’d never seen in a man before.

Suddenly, the “little things” whose absence I’d once lamented were part of what we shared — flowers for no reason, unexpected phone calls, expressions of love.

But sadly, all of this came as I realized receiving Larry’s affections without being able to commit to him was selfish and unfair. After giving so much to our relationship, he deserves more than the emotional limbo I’ve led him into.

In an email today, Larry indicated the door is still ajar for yet another reprise between us. As much as I miss him, though, and wish I could ignore what is standing in our way, I don’t think we can reconcile.

* * *

February 7th, 1997

Larry and I emailed back and forth last week and I called him a few days ago. As always, he was full of love and understanding. He said he still wants to be my best friend, that no matter what he wants to be part of my life.

“Not a day goes by that I don’t thinking about you,” he said softly.

“I miss you,” I said.

“I miss you too,” he replied.

It was a wonderful, comforting conversation, one that made me hopeful about the possibility of us remaining in touch.

* * *
Larry and I would indeed stay connected. And my post-breakup blues about us would soon be lifted by the return of an old flame, just in time for Valentine’s Day.

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May 25th, 2009 — 4:30pm

When it comes to May-December romance, I’m about as intimately acquainted with it as Mr. and Mrs. Kutcher.

Ashton and Demi: the poster couple for May-December love

My first two boyfriends were 16 years older than me. And my late and much-loved parents (who adored each other) had a 25-year age difference between them.

For as much, though, as I’ve always been and continue to be drawn to older men, I know the May-December dynamic isn’t for everyone. And that in some cases, it’s downright creepy.

Take, for example, the sixty year old guy who recently emailed my 25-year-old friend Diana through a dating site — eight times. In his ninth attempt to make contact, he asked why she wasn’t responding to his messages.

“Sorry,” she said politely. “I think our age difference is too steep and I’m just not interested. Thanks, though, and good luck!”

His response, as another friend of mine quipped, suggests he hasn’t dealt with rejection since the Reagan years–

“I’m surprised that someone who claims to be so sweet would make a nasty, gratuitous comment like that. A simple no would have been fine. That comment was very nasty for no reason. But I feel better as I never want to be with a mean person and that was, needlessly, mean. I bet I still see your [profile] for a long time.”

I guess even among the AARP set, ettiquette is fleeting in cyberspace.

Up next…drinks with a member of NY’s Finest and Single Gal In The City–the book?

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May 25th, 2009 — 11:30am

When it comes to May-December romance, I’m about as intimately acquainted with it as Mr. and Mrs. Kutcher.

Ashton and Demi: the poster couple for May-December love

My first two boyfriends were 16 years older than me. And my late and much-loved parents (who adored each other) had a 25-year age difference between them.

For as much, though, as I’ve always been and continue to be drawn to older men, I know the May-December dynamic isn’t for everyone. And that in some cases, it’s downright creepy.

Take, for example, the sixty year old guy who recently emailed my 25-year-old friend Diana through a dating site — eight times. In his ninth attempt to make contact, he asked why she wasn’t responding to his messages.

“Sorry,” she said politely. “I think our age difference is too steep and I’m just not interested. Thanks, though, and good luck!”

His response, as another friend of mine quipped, suggests he hasn’t dealt with rejection since the Reagan years–

“I’m surprised that someone who claims to be so sweet would make a nasty, gratuitous comment like that. A simple no would have been fine. That comment was very nasty for no reason. But I feel better as I never want to be with a mean person and that was, needlessly, mean. I bet I still see your [profile] for a long time.”

I guess even among the AARP set, ettiquette is fleeting in cyberspace.

Up next…drinks with a member of NY’s Finest and Single Gal In The City–the book?

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March 7th, 2009 — 7:37pm

In a long distance relationship, you have to work twice as hard to stay together — especially when there’s a 16-year age difference. That struggle intensified as I approached one year of dating my California-based sweetheart Mark (a.k.a. Sparky).

After two tumultuous encounters back to back, we decided to start dating other people. The tricky part — though this was understood, we never explicitly talked about it.

As the younger half of our May-December romance, I was craving a male distraction of the local variety. Sure enough, during the second half of my senior year in college, that’s exactly what I got. I now Open The Vault to Volume #57 and take you back to the spring of 1995…

March 7, 1995
Mount Holyoke College,

South Hadley, MA

Dear Diary,

I had a date tonight with Dave, a DJ I met last Friday at a campus party.

Amazingly enough, I actually had a good time — he’s cute, funny and impressed with my vocabulary. I even enjoyed the goodnight kiss. He was polite enough to ask if he could kiss me.


: My beloved alma mater was the backdrop for an unexpected senior year romance

“Could I make a strange moment any stranger?” Dave quipped, before leaning down to lock lips. He’s tall too — a nice change from Sparky.

I realize that a lot of what made tonight enjoyable was that I wasn’t overanalyzing every little thing that happened. I have a bad habit of doing that with Sparky.

We spoke today.

“What’s on your mind?” he asked.

“Can’t I just be calling to say I love you without an ulterior motive?”

“No,” he said with a laugh. “I know you, you’re pondering something.”

I was — the possibility of going to LA next month.

Sparky lamented about his financial situation, mentioning the recent $500 bill from our Valentine’s excursion to The Poconos. I thanked him again for the trip and he said–

“I have to save for graduation.”

He made it sound like this milestone in my life was special for him too. Like he has every intention of being there.

* * *

March 13, 1995

I had a great time again with Dave. He had me laughing quite a bit — and also wondering if there’s anything left to salvage between Sparky and I.

After a movie, Dave suggested we go for a walk on campus. We sat on a bench by the lake. He took my face in his hands and kissed me, eventually nibbling on my neck and earlobe.

As he put his arms around me and took my hand in his, Dave told me I’m terrific and incredible. When I returned the compliment, he said–

“That’s because I’m kissing you.”

Back at the dorm, there was a message on my machine from Sparky. I called him back and he asked where I’d been. I lied and said I was out with a girlfriend. I felt kind of duplicitous, but it’s better than feeling miserable — which is what I’ve had enough of with Sparky.

* * *

My romance with Dave ended up getting me through more than just the long-distance blues. Dave would be right by my side when carelessness on my part led me to a brush with death.

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