At an Awkward Age When Women and Their Moms are Both Hot
Vacationing on California’s central coast has reminded me I’m at an awkward age when women and their mothers can both be hot. I’ll turn my head for a 40-something mom one minute, then check out a 20-something sexy daughter the next. (I have no problem with older men dating younger women, at least if the man is me.)
Which reminds me of a New Years Eve in Manhattan a few years ago. I was out on the town with friends, all of whom were coupled up (and none of whom were matchmakers.) Late in the evening I ventured alone into the restaurant bar. I sidled up to two attractive women and chatted them up over drinks. They looked so similar – their eyes, cheekbones, noses, smiles – I asked if they were sisters.
“Yes!” they said in unison, clearly pleased I’d made the connection.
But their grins and laughter hinted at something else. Turns out they were a 52 year-old mom and her 26 year-old daughter, born in Venezuela and living in New York. (Hey, it was dark, we’d been drinking, they swore their family never aged. Plus, the daughter confessed the mom had had some work done.)
They were both fun, flirty, and sexy. But the more we talked, the more I felt the daughter was more my type. She was educated and career minded, loved that I was a dad, and said she wanted a child of her own someday. (Something I was still entertaining a few years ago.) The mom, on the other hand, had been married four times, was long past dealing with children, hated work, and was used to being a kept woman.
From that point on, I made my moves on the daughter.
Problem was, the mom liked me a lot. And the daughter felt duty bound to make sure her mom’s happiness came first. (It might seem the daughter simply wasn’t attracted to me. But there were tons of guys trying to hit on her all night long, and she kept wrapping her arms around my neck, giving me kisses and hugs. Then again, maybe she was just drunk. Who cares? It was New Years, it was fun.)
On the dance floor, I pulled the daughter close and professed my undying love (okay, lust) to her and invited her to spend a week in California with me. (I’d blame that invitation on New Years drunkeness, but at my age, I figure we live in a global village. You work with what comes your way.)
The daughter loved the idea! She’d never been to California and really wanted to come out. But once again, she suggested I extend the invitation to her mom.
“Don’t you like my mom?” she asked.
“Sure,” I said. “But I like you more.”
“But my mom needs a man to take of her.”
“She’s already had four husbands. You need a man, too.” And I needed feminine energy in my life.
The daughter pressed close and placed her hands on my chest. She looked up at me with bedroom eyes. “You know,” she said, “I loved all my step-fathers very much. And I will love you, very much, too.” She raised a flirty eyebrow and flashed a knowing smile.
I got the feeling her step-fatherly love wasn’t platonic.
Perhaps I should focus on the in-between looking women, the ones with moms who are eighty, or daughters who are two. (Then again, a mom-daughter threesome might be fun… just kidding!)
Like I said, I’m at an awkward age.








Comment by mama llama
| July 25th, 2008
Three words: ay ay ay.
Your mention of needing feminine energy in your life struck a real tone with me. Energy from a partner is of utmost importance; it can create a symbiotic bond that allows you both to grow, dependently and independently. When only one half of the couple possesses the “energy”, as in my situation, the relationship will simply stagnate.
And to grow together as opposed to a one-sided care-giving, purse-padding and bed-sharing dependency would, I tend to believe (perhaps naively), rock both’s worlds.
The threesome possibility…JA! Funny…from the way you told your story, I got the impression that they had already been down that road!
Nice story. Have a great Friday! Be well.
Comment by Hip_M0M
| July 25th, 2008
This is too funny but what will be awkward for you – sorry to bring this up – is when women your daughter’s age start becoming attractive to you…sooner than you may think!
Comment by Lance
| July 25th, 2008
I’ve approached two sets exactly like this, hot mom/daughter combos where I thought they were sisters. I’ll be quite honest, I was more attracted to the mom each time, even though I was much closer in age to the daughters. The daughter was “hotter,” but the mom had a sexier vibe. I think I’m developing a MILF/cougar fetish. I’ve been flirting with a MILF via text lately and can’t wait to meet her.
Comment by Tonya
| July 25th, 2008
What an awesome story!
My mom and I are like this. People have always thought we were sisters. As a matter of fact, my mom even went out with me and my guy friends many times in high school. She was the coolest mom ever and all of my friends loved her. I have to admit, it was from watching her that I learned how to flirt. She used to flirt like MAD with my soldier back during our high school days when he would come over as my friend. She’s pretty excited that we’re really into each other now.
I don’t know. Since I didn’t start having children til I was 31, I’m not sure how it’ll look when my daughters are in their mid-20’s and I’m in my mid to late 50’s. Then again, my mom is still stunning at age 59 so….
Its fun to hear your insight to the things that happen in your life. Thanks for the perspective!
Comment by Honey
| July 25th, 2008
hahahahahaha! I love this story, DM…
Comment by mad cartoonist
| July 25th, 2008
Sorry to tell you, but I think the joint heavy flirt was probably just them having a little fun with you.
Especially since I noticed that you stopped the story before saying what (if anything!) happened next…..!
I’m guessing they made excuses and booked it out of there, leaving you panting. If not….do tell!
Comment by lisaq
| July 25th, 2008
Haha…what a crazy story. I go out with my daughters often and we always get the whole ‘you look like sisters’ thing. We get a kick out of it and enjoy the interactions though some of them get a little weird sometimes but it’s all good and we enjoy the interactions.
Lance, I definitely think you are developing a Cougar fetish. How fun for some lucky Cougar!
Comment by dadshouse
| July 25th, 2008
Tonya – I won’t flirt with young girls, so my daughter’s friends have nothing to fear.
Mad Cartoonist – As for what else happened that night – we stayed out ALL night (which isn’t a big deal in NYC, but is something I haven’t done in Cali for a loooong time). I suggested heading back to their apartment that same night, but the mom said no and gave me her phone number instead. She wanted me to ask her out on a proper date. (I can’t blame her.) Bottom line – I took an early morning cab back to my friend’s apartment, and didn’t see the Venezuelan women again.
And yes, they could have been playing me for free drinks. I don’t mind too much, I had fun clubbing with them.
Comment by America
| July 25th, 2008
Maybe you should stick to MILFs with sons, might be safer!
Comment by The Exception
| July 25th, 2008
Sounds like it was a new year’s to remember!
Comment by singleworkingmommy
| July 25th, 2008
The daughter said WHAT? Ew!
Comment by Single Mom in New England
| July 25th, 2008
Being 39, for the first time in my life, I find myself being attracted to men at both ends of the age spectrum. I just saw “Mamma Mia” tonight, and couldn’t help lusting after BOTH the “older” male leads (Pierce Brosnan and Colin Firth) AND the young 20something hottie that played the younger love interest. (Sad when I’m old enough to be his mom!) So I’ll stick with Pierce and Colin. Older men have more “experience” anyways. ;)
Comment by MeAgain
| July 26th, 2008
Dadshouse mate, it’s gonna get worse what will the myriad of anti-ageing products and cosmetic services available to all women nowadays.
Pretty soon you will find yourself lusting for a 60 year old granny, her 40 year old daughter, and 20 year old grand daughter.
And you won’t have a clue how old the two older women really are due to all the ‘work’ they’ve had done.
;-)
Comment by single venezuelan mom
| July 26th, 2008
Perhaps… they were both having a great time! see.. in Venezuela the hunting game is always on – we know how to flirt,,.. but at the end… we decide if we want the man or not. Like my grandma said ” The man ask,.. but the woman decides!..)…
funny!!
Anyways.. life is just one… so those moments are priceless.. so why not enjoying them and laugh…
Comment by QTMama
| July 27th, 2008
*giggle* Manwhore!
Just kidding pumpkin. I heart you.
Comment by pajama momma
| July 27th, 2008
The daughter said WHAT? Ew!
Yeah, I’m with singleworkingmommy here. That’s a little gnarly.
Comment by Cathouse Teri
| July 28th, 2008
Gosh, I thought guys were always at that awkward age. I mean, once they are over twenty. I know my son’s friends are always teasing him about taking me out. And then he punches them in the face. :)
Once, when I was out with my daughter, a few guys in their twenties approached her. She laughed and said, “Oh, I’m not available, but my mom is!” She proceeded to go get me from the table and bring me to the bar to meet them. The three of them spent the rest of the evening with me, doing body shots.