Expectations vs. Reality: Dating Somebody Older Than You

It sounds good in theory. After years of toiling in the shallow end of the dating pool, the idea of going out with an older (and presumably more mature) person seems enticing. The media doesn’t help this notion. Movies and television shows have gone to great lengths to portray May-December relationships as the holy grail. Whether it’s films like The Graduate or Wedding Crashers, or even songs on the radio (yes, Stacy’s mom has got it goin’ on), the idea of dating somebody older has constantly been portrayed as a mystical, passionate opportunity you’d be a fool to miss out on. In reality, these relationships are more complicated than you might assume. These are the expectations and realities of dating somebody older than you.

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Expectation: Older Means Wiser and More Mature

Reality: Older Means Same Maturity and Fewer Excuses

Expectations say that when somebody is dating a person who is older than them, usually the older person will be the more mature of the two. In reality, this is hardly the case. Most of the time, older people will date younger people because of their own immaturity. Have you ever heard the idea that girls mature faster than boys? It’s true and these relationships are proof of that.

Expectation: Spending All Day in Bed in the Throes of Passion

Reality: Spending All Day in Bed….Period

It’s an old joke. Dating somebody who is older (aka a “cougar”) results in lots of great sex, right? That’s what all the movies and television shows say. Unfortunately for our hormonally-charged friends, this is rarely the case. Yes, older people like sex just as much as younger people do, but it’s not their lifeblood. There’s no magic trick one develops as they grow older that makes sex better. They might become less selfish, for sure. But that’s the only “trick” there is.

If you find yourself spending an exorbitant amount of time in bed, it’s probably because you’re both too tired to do anything but binge Netflix shows or Lifetime movies.

Expectation: A Lifestyle of the Rich and Famous

Reality: Nobody Can Even Retire Anymore

Our economy kind of sucks right now. The idea of “marrying for money” isn’t totally obsolete (yet), but it’s not as easy as the movies make it out to be. Very few people are actually super rich. The assumption that younger people marry older people for the money is not necessarily the case. Many of the older people in a relationship can’t even afford to properly retire these days, so those who date older people likely do so out of love.

Expectation: Trophy Dates and Gala Events

Reality: Local Bars and Passing Judgment

We’ve all seen this scene, or something like it: Anna Nicole Smith pushing her wheelchair-bound husband down a red carpet, or Ashton Kutcher sharing a kiss with Demi Moore at a movie premiere. Younger people at the arm of somebody older makes for an unusual but extremely photogenic moment.

Unfortunately, for most of us, it’s not red carpets or fashion shows that serve as our evening’s entertainment. Most of the time, it’s a local bar and the lights are dim and nobody actually even really cares.

And that’s the biggest reality check we can take from these relationships: nobody actually cares. So feel free to love who you want.

 

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5 Benefits of Dating an Older Woman

Why You Shouldn’t Shy Away From Dating an Older Woman

Some people, especially those in relationships with significant age gaps, like to say that age is just a number. Of course, this is true: When it comes to relationships where one partner is significantly older than the other, it’s not age that matters most. Instead, it’s all those other little things — shared hobbies and goals, similar temperaments, mutual respect and understanding — that typically determine whether or not a partnership between two people is built to last.

Older men have no problem dating younger women, and the opposite dynamic of older women dating younger men is becoming more common, too. But why? Why would a guy seek out a woman who is five (or more) years older than him? Maybe it’s because they’re in on a little secret that you haven’t quite figured out for yourself yet. If you can’t already guess, there are a lot of benefits to dating a more “seasoned” woman.

If you’re still skeptical, let these relationship experts impart their knowledge upon you. You’ll be a firm believer in no time.

She’ll Likely Have a Wider Worldview

With age comes experience and wisdom, which is precisely why we often turn to those older than us for advice about everyday problems. They’ve been around the block, leaving them equipped with plenty of knowledge that can change a younger person’s viewpoint on whatever issue they may be facing. The same applies in a dating context.

“Some older women are more sophisticated than younger women because they’ve had more time to experience life,” says relationship expert and author April Masini. “They know about more things than younger women might, and they have a lot to offer because of this wealth of experience. The conversation is going to cover a much broader swath of life than it might dating a younger woman. For someone who is just starting to date older women, their points of view, and the way they see the world may be new, fresh, and exciting. This new perspective will affect a man who is sensitive and attentive — he’ll acquire an expanded sensibility and he’ll have the benefit of her experiences.”

She’ll Already Be Financially Secure

As Chicago-based dating coach Tripp Kramer explains, the older a woman is, the higher the probability that she has her financial house in order.

“This is because she is either a) later in her career, (at which point) people generally make more money, or b) she has been through a divorce, which can also grant her more money,” says Kramer.

This isn’t always a done deal, of course, but there are older women out there looking for a young stud like yourself that they can dote on. According to Masini, “When it comes to money, older women dating younger men may be looking for someone they can take care of and mold. Other women may be looking for a younger man who has his own money; it really depends on the woman.”

She Knows What She Wants and Will Be Honest About It

Younger women, like younger men, are often still trying to figure themselves out — what they like, what they don’t; who they can see themselves with; what things in life matter most to them. Older women typically have these things figured out already.

“Because they have more life experience, older women usually don’t want to waste time when they already know what they want,” explains Masini. “They’re usually quicker to make decisions than younger women, who are still deciding what they like and don’t like.”

Emyli Lovz, a San Francisco-based dating coach for men, shares a similar sentiment. “She’s likely been down the rabbit hole of a bad relationship or two,” she adds. “She knows what she’s looking for and doesn’t want to waste her time on the same old guy again. Keep in mind: patterns are hard to break for anyone, so she might be avoidant at first, if you’re not her typical type. In these cases, it’s best to get good at overcoming objections.”

She’ll Have Plenty to Talk About

Growing up a generation apart, or even just at opposite ends of a particular generation, nearly equates with growing up in different universes. Because of this, conversations with an older woman provide an opportunity to expand your perspective in ways you otherwise wouldn’t.

“Assuming that you’re referring to women who might be 38 to 45 … you should have deeper and more meaningful conversations compared to dating a 22-year-old woman,” says Lovz. “She might be more versed in what happened in the real world while you were still in high school or even junior high.”

In fact, Lovz believes that “differences in age are similar to differences in culture,” explaining how what she’s gone through can help you get through any hardships of your own.

RELATED: Pros & Cons of Dating Older Women

“They’re an opportunity to expand your perspective and step out of your own reality,” she adds. “Her experience can help you better understand various stages in your own life, too. She might be particularly helpful with transition periods like moving into a new role at work or navigating the purchase of your first home, if she’s already had life experiences like the ones you’re going through.”

She’ll Probably Have a Solid Amount of Sexual Experience

While it’s tough to generalize, older women will typically bring many years of sexual experience into a relationship with them, and there’s a good chance they will be able to teach you a thing or two in between the sheets.

“Generally speaking, the older she is, the more sex she has had,” explains Kramer. “So, if you are interested in kinkier types of activity or want to explore more of your sexual side, then it could be a great opportunity.”

If you’re looking to date an older woman, there are a number of places to meet one. Whether through friends or work, at a hotel lounge or upscale bar, through yoga class or via an app or website — wherever you may run into an attractive older woman that peaks your interest — don’t be afraid to see where things lead.

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Mary – Chapter 5 – Sunday, Funday

Another tale of one man’s journey navigating his way through the dating scene in Philadelphia.

I text Mary and ask her if she wants to have a drink with me on a rainy Sunday after four when I finish up at the salon. She agrees. She wants to hear the crazy story about Marisa because it all happened at the restaurant where Mary works as a hostess. (See Marisa – 2017 to Present – The Friendly Hostess) 

Mary and I like to hang out and drink, but we’re trying to keep our costs down. I suggest Doobies. She’s down for that. We meet at 22nd and Walnut. Umbrellas open we walk south to 22nd and Lombard.

Doobies is a bar that’s been in the neighborhood for a long time. It’s sort of a dive, but the food is good, and the drinks are cheap. There are all sorts of artifacts on the walls like any other dive. But the big theme there is David Bowie. There are pictures of him throughout the bar, and plenty of Bowie on the jukebox. Oh, and they only take cash.

We arrive, and the place appears to be closed. But it’s 4:30 on a Sunday, and the door is unlocked. We go inside to get out of the rain. I see a phone on the bar, and I call out hello a few times. Then some guy comes up out of trap door in the floor behind the bar. I greet him, and he says that she’s not here yet. I don’t know who “she” is, but it said they open at 2pm on Sundays. He says she normally gets there around 5pm.

Mary doesn’t feel like waiting around for a half hour. We thank him, and I tell her I have another plan. We go to South street, and walk over to 21st. Ten Stone is a bar there. A bit nicer than Doobies, but on a rainy day, we’ll settle. It’s a little noisy, because some young people are playing pool and darts in the next room. But it’s not too bad. It’s a nice crowd and the server is friendly.

Mary goes with red wine. Good choice on a chilly, rainy day. I go with some sort of hoppy beer and a shot of whiskey. It’s just been that sort of week. Just the stress of working at the institute, dealing with Marisa the other day, and just everything else that is exhausting me lately.

I tell her all of my stories and after a while I’m feeling much better. I don’t know if it was me telling Mary what my week was like, or the whiskey knocking the edges off. Probably a little of both.

The table where we were siting was small. It was a high top against a wall. We were having a great time laughing and talking, and I was a little worried about Mary’s wine glass.

Have you ever been out at a restaurant, and you just get that vibe, or that premonition that you feel like something’s going to get dropped, knocked over or spilled?

Well I got that feeling early on, and didn’t Mary knock over her wine? I knew that thing was going over. It splashed on her shirt, but didn’t completely empty the glass. She actually got one last mouthful out of that glass, before heading to the restroom to clean up.

She seemed a little buzzed. She got buzzed like this before that Pollyanna holiday party, two weeks ago. I needed to take charge of this situation. So while she was in the bathroom, I paid the bill, and called her an UBER. Normally I would be crying about having to pay the bill, but I dig Mary, and she always pays when we go out. Maybe she’s tired or drinking on an empty stomach. She comes out, and it looks like she got the wine stain out before it could set.

I put her in the UBER and send her home. I tell her to text me when she gets home, so I know she arrived safely. The rain has stopped and I’m close to home so I just walk. I light a cig, and reflect on the evening’s events.

I get home and I have a text from Mary, saying she’s home. Another Sunday down.

 

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Clarice – Chapter 4 – Champagne Lady on a Beer Budget – Part Two

Another tale of one man’s journey navigating his way through the dating scene in Philadelphia.

Yesterday we left off here:

She shows me her profile on OKCupid, another dating site. She wants me to read her profile. It’s actually really good, it shows a smart, confident, independent woman. I like that. “That’s why men are intimidated by me.”

“I can imagine. But I dig a confident woman. Especially one as pretty as you.” The picture she has posted of herself is spectacular. She looks like a gorgeous woman in her forties. I notice the age posted on the profile says she’s fifty-six. I point to this and she laughs and says, “That’s my OkCupid age.” I laugh and get it. She looks great and ratcheted back her age five years. “I’m really impressed with that pic of you, Clarice.”

“Cause my tits look so good?”

“Umm… well, yes, but…”

“That’s pretty much all I got to offer. I got no ass! I got skinny bird legs!”

“I’ll be the judge of that.” I say, smiling slyly.

Here’s the great thing about dating older women. They are over all of their body issues. They don’t give a shit about all of the nonsense that clogs the heads of younger women. like her profile says: “I know what I can, and cannot do.”

We’re slowly munching through the tacos. She seems to like them. I order another Tecate. She starts looking at the wine list. (Here we fuckin’ go…) I can’t MAKE her drink tequila if she doesn’t like it. I tell her it’s okay to have a glass of wine. (I know! There goes ten bucks!)

She asks me about my artistic background. I tell her about my art and musical background. (I don’t want to epand on that here. That’s for future posts) She asks if I do anything artistic now. I tell her I do some writing.

“Has anyone seen it?” she says.

“No.”

“You should write a blog.”

“Really?”

“Sure! You know about all of these things around the city. What to drink, where to go, and what to do. It would be really interesting. You could even write a blog about dating. I’m sure it would be fun to read!”

“Do you really think so?”

“You should look into it.”

“I’ll see what I can find out about blogging.”

(Oh, the irony!)

Time goes by and she’s getting a buzz on. She starts getting a little affectionate. I ask her if this okay with her PDA rule in place. Apparently it is, because she kisses me again. She’s canoodling around my ear and neck. “Oooh you smell good!” (She’s into me. It’s so on.) “What is that you’re wearing? It smells sooo good!” I tell her I forget what fragrance I grabbed out of the vanity this morning. Maybe Aqua di Gio, by Giorgio Armani I tell her. (Bold faced lie. It’s Axe body spray, Phoenix)

She kisses me again. “Don’t you ever use tongue?” she hisses. “I do…” I look into her eyes, and then at her mouth and then look downward, then back to her eyes, just so we’re clear. I tell her when I kissed her at the Ritz on Saturday she seemed a little tight-lipped. She says she was right there ready for anything. Got a live one here. Maybe it was the tequila talking. Clarice has no idea who she’s dealing with here. Like a baby seal hopping into the water to cool off, just as the grey dorsal fin cuts through the water heading right for her. She kisses me again. Now her lips feel softer and more passionate than Saturday. I can tell the difference. She’s been thinking about me.

She orders another margarita. (Thank you!)  I’m feeling good and into my third Tecate. It’s nearly seven. Need to wrap this up soon. I promised Church I’d meet him at Sofitel. She starts talking about the Comcast Holiday show they do on the digital wall in the lobby of the Comcast tower. She asks me if I’ve ever seen it. I told her I saw it a couple of years ago. (Probably with Michelle and her mom.) She says we should go see it. I tell her I think it’s over by now. She looks it up in her phone. It was over the day after New Years Day.

“Aww too bad, I thought we could go see it after this. See? I’m trying to think of free things we can do together!” (points for that)

I apologize that we missed it, and also tell her I have to go meet with Church after this. He has some important stuff to cover with me.

“Oh…You’re always fitting me in! On our first date at Panorama you had to leave.”

“I had our annual holiday toy drive at Time for the kids at CHOP!”

“On New Years Eve you had to leave me again!”

“I promised my friend Carly weeks ago that I would help her set up a New Years wedding party!”

“Now you’re fitting me in around your friend!”

“He’s having some domestic issues, and my friend needs my support. We set this meeting up a before I made this date with you.”

“Oh…okay. I’m sorry.”

“No worries. I really like you Clarise. I want to see you, but I’ve had a lot of things going on over the holidays. I know now that they’re over, it should free up some time for us to be together.”

“My birthday is coming up, you know. I’ll be sixty-two on January 15th. Martin Luther King’s actual birthday, not the day we celebrate it. Do you have to work that day? It’s a Sunday.”

“Normally I do.”

“Well, here’s what I think you should do; switch with someone. Get on the train. Come out to Upper Darby around 1pm and I’ll pick you up and bring you to my house. You can stay until whenever you have to leave.”

“That would be great. I’ll see what I can do.”

Correct me if I’m wrong, but I think Clarice is making it clear she wants me to come over and make love to her. Which I am prepared to do. I like Clarice, and I want her.

The check comes. She had two margaritas, one glass of wine, and three tacos. So technically, not including tip, she will have only cost me twenty-three dollars tonight. Please don’t think I’m cheap, dear reader. If you have been reading this blog, you’ll know that I have spent thousands of dollars wining and dining all of these women.

We walk outside and she takes my arm. I walk her to her subway stop. I walk her down to the first landing and kiss her. She’s surprised and pleased. I offer her what I did not before in a kiss. She smiles and kisses me back.

I hear the roar of the approaching train. Time to go.

 

Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every Monday, Tuesday & Wednesday at 8am EST.

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