January 18, 2020

10 Lessons in Love: Dating an Older Man.

Too often, the “Bogie-Bacall” reality is simply an old-fashioned fantasy that plays into perpetuating what a woman’s role is in society today.

In the wake of the reemerging Weinstein trial, as well as with respect for the continuance of “Me Too,” I wanted to provide a safe place for a dialogue to convene concerning women who are “swept off their feet” by a charming, older gentleman.

“Love is love” and “live and let live” ring true, especially for this discussion. This commentary is not intended as a critique, but rather to illuminate us to the possible ways we may be unwittingly compromising our values and belief systems as strong, independent women.

Be proud to earn your own way in this World; it is very brave.

1. Try not to focus on what others might think.

This might seem obvious, but my inclination is that most outsiders commenting on an age gap in a relationship do so from a place of genuine concern, not necessarily malice. Consider it as a nice sign that people care about us and want what they think is best for us, but we needn’t take their opinions too hard to heart. We can let our own hearts be our best guide.

Perhaps there is some common ground settled between the difference in age that will convince any naysayers that in the end, all that matters is that two people are happily in love. However, we can hardly expect to become too upset if our friends and family express their fears openly, especially early on. If this new guy does turn out to be a creep, abuser, and/or user, it will probably be over by next Thanksgiving anyway.

If there is a happy ending, at least our parents will be long-forgiven and swiftly understand their misgivings before they get grandchildren.

2. Be assertive.

Too often the youth and naïveté in a May-December invites an imbalance of power and decision-making to the relationship dynamic. Whether it’s a comment about “life experience,” previous relationships, or simply the fact that someone younger might not be as forthright with advancements in the sexual department, there will inevitably come a time in the companionship when each other’s needs will be questioned. We have to stand up for ourselves! Remember, just because they’re older, it doesn’t always mean they’re wise.

If anyone ever makes the situation into a power struggle or deliberately forces the age/experience card to “win” an argument or a compromise, run, don’t walk for the door. 

3. Examine the relationship from the “outside.”

If we are not able to directly ask our partner, “What is it we are doing here?” then it is probably best to exit the situation as gracefully as possible. Constructive, open, and flagrantly honest communication is the foundation of any healthy connection, and it is definitely okay to want to know what is intended by someone wanting to spend so much time with us.

If all that is accomplished as a couple is fighting about what the other person wants/needs, and then having wild makeup sex, it might be time to find someone else who has an easier time being open and honest with us.

When observing the relationship, does it seem like those two people are compatible in the long-haul, or is it an obvious case of fanning flames? If it is, let’s check the exit sign and stop lighting life up with more drama. There are way more exciting ways to make waves, and they involve far fewer hurt feelings and confused hearts in the long run, too.

4. Be prepared to be in a different place financially.

For some women, this may not be the case, but many times when we elect to date “ahead,” we do so out of our initial attraction to their allure and sophistication. These are attributes we may want to cultivate within ourselves in our own right, so we have to try hard not to become too competitive or resentful when it seems to be happening faster for the person we are with. Especially if they have more than 10 years on us.

If, on the other hand, we give ourselves time, we too will enjoy the hard work and dedication that putting off the distraction of relationships allows. Later-life dating reprioritizes intense energy on putting our careers, schooling, or any other championing endeavors first. Resist spending too much time in bed with a guy who prioritized himself before finding love; it means that all of his hard-earned success is his and his alone, at least up until the place in the story where the two people meet.

This is a different scenario than two people working simultaneously and supportively to carve out a niche of their own as a team/partnership. It’s definitely a choice and sacrifice to have the lone wolf mentality (leaving finding “the one” up until later in life). It’s a trade-off.

One scenario makes it much more enjoyable to be in a place of confidence and stability—“ready” for our partner to enter our lives—and the other option makes space for someone else ahead of time, the perfect place for the two of us to grow something together. Neither way is “better.”

A note about the allure of bachelors, though, because anyone who only enjoys the flashy attention that comes with procuring a beautiful date, but has no real interest whatsoever in anything beyond showing her off, or taking her home, is downright degrading her sense of worth. If any partner is unsupportive or diminishing of a woman going after her dreams, or spending more time away from home to work on building a business or career, then that person is not worth even a second take of her time, let alone the best-dressed days of her life.

5. “If we were a Hollywood item, would we be tabloid fare or fodder?”

Dating someone who always expects us to be around for their emotional support means there are going to be a lot of paparazzi pictures of the two of us grabbing coffees. Is the latest story painting us in a good light, or is it spinning the 25-year age gap into a web of gold-digging lies?

That is the most common misconception, isn’t it? “She’s only with him for his money.”

Well, what’s he interested in, then? You know what I’m talking about. We can’t help but think things like, “Hmm! 38-year age difference. Wonder what she saw there?” or, “Come on dude, grow up, you have a daughter older than her!”

Can we all stop playing into this stereotype, please?

Women, we have the power to stop making it okay for any old man to grab away a youthful sprite, lock her in a mansion somewhere, and galavant around the globe with her freshly-picked peach when weather and working conditions permit. Ego-driven men love nothing more than having a hot, young piece of bikini bottoms, and of course, expect her to remain eternally ageless and delightfully trim at the whim of his every need, forevermore. Ugh. Puke. Sometimes, I really wonder if the only attractive option turning the blood red for men these days is something young, buxom, and beautiful, but sadly, I get it.

Women have hormones, too. I have just aged away from the subterranean notion that gorgeousness equates to “eternally 28 in my face and the silicon’s just for you!

The plumped-lip, popped-booty with a fresh-out-the-clinic boob job look is just plain wrong.

Hey ladies, we do not even grow into ourselves until we are at least 35, which, by the way, is not even that “old.” Our 30s, 40s, 50s, and beyond are something incredible to look forward to. Our baby faces will have revealed chiseled cheekbones (I can already see mine more vividly) that put even the most photoshopped couture magazine covers to shame, and we also have our own careers, routine, everything that we do just for us—it’s all nailed-down. This confidence is everything.

Be the woman who waits to meet her champion, or at least be with the man who stopped texting 22-year-olds when he’s pushing 50. In fact, I’ll put it this way: men, take up any more of her time and she’ll never get the chance to work on being the woman who she wants to be. I would personally much rather read a story about a perennially single Queen who waited for her King (a la Amal and George, perhaps?) versus a trite little tale about two-timing Princes. Those creeps keep their eye on the prize and think everything is the next best thing. Sad.

P.S. Amal certainly makes the case for the age-gap working later on in life. Perhaps it really is true that women are light-years ahead of the male chromosome, maturity-wise. In either case, it doesn’t actually matter. Age really is only a number. But! I am genuinely blown away by the sheer magnitude of men over 40 who imagine an 18-year-old to be interesting beyond her youth.

6. Try to see your partner’s perspective.

Imagine having suddenly transformed into the apple of our eye.

What do they think of us?

Imagine all of the reasons why this person likes us so much that they want to spend the majority of their waking hours with us. Or, do we feel like we are just the first person they think to text/call when looking for a convenient distraction away from their messy, ill-ridden life? Don’t be the trash can. They do not get to dump all of their problems into us and expect to take the easy way out.

It might be hard to tell right away, but if someone is using you, have the courage to walk away. We do indeed deserve a genuine connection, and part of that involves having a caring individual who wants to get dressed up and head out with us every once in a while. (Refer back to “Be assertive,” number two above, if ever in doubt.) Sometimes, all it takes is communication to decipher the clues as to what someone else is really trying to tell us.

Lastly, always remember that we are, of course, so awesome; obviously, this person is into us for a reason! Just try not to waste too much time if this person is only interested in the outside. Someone else might be waiting for us, someone who loves our beautiful mind just as much as how great our butt looks in yoga pants, or our bedhead, or the way that we smile.

7. Have an exit plan.

If it turns out we are being taken advantage of, let’s make sure we have a solid exit plan in place. Here are some considerations we can make for ourselves:

a) Have a “safety net” in reserves.

If we are living together and/or financially dependent on this other person (the “breadwinner” perhaps), we have to have a way out that only we know about. Maybe it means stashing a few thousand dollars in a savings account or investing some money somewhere that only we have access to, or sending some money to a loved one we can trust in the event that anything ever goes south between us and our paramour.

b) Have a place to go if it gets bad/ugly.

The bruised wife phenomenon is when an abused woman continues to retreat back to the boxing match for another ride on the merry-go-round of madness because she doesn’t know where to turn or what to do with herself anymore.

No matter who we are seeing romantically, we must keep in contact with friends and family. This gives us a chance to pick up on any red flags, especially the flag that signals someone is trying to cut us off from receiving external support. This tactic effectively makes us dependent on our partner as the sole source for emotional validation. (If ever in doubt, refer back to number one above.)

If spending time with friends and family to regroup after a breakup, try not to let it appear as a failure. Staying in the situation that made us feel trapped is way worse for us in the long run, but the sooner we can escape, the faster we will heal. That doesn’t happen alone.

c) Who are we without this relationship?

Maybe we are the girl who sings in the shower or does yoga in the kitchen with a green juice, or maybe we like to drive fast cars, or skateboard, or record music, or dance so hard our French braid falls out. Maybe we like tofu in our Pad Thai more than meat, or maybe we just realized, damn, I used to really like me before this relationship, too. Well, great time for a wake-up call then.

Set boundaries, pack bags, slowly transition away from the situation. No matter what, keep breathing. Stay true to what feels right, even if everything seems lost. There is always a way out. Always. 

8. Make some raw peace with all that.

I used to get teased on the daily as a kid for having red hair. It gave me a thick skin. Thankfully, as an adult, my karma has been getting fawned over at the grocery store by ladies who ask me how I keep it so long, shiny, and healthy. That little fifth-grade girl who always got picked last for “Red Rover” is certainly laughing her little snow-panted a** off now!

If anyone asked me today if the “carpet matches the drapes,” I’d simply shrug and ask them, “Does yours?” Maybe with a wink. I love my red hair, and am proud I withstood the bullying and never dyed it blonde a la Lindsay Lohan circa 2004. (P.S. Thanks, Mom.)

Aside from the universal truth that middle school boys are perverts, my point with this is that we probably have had some moments in our lives that mortify us when we think about them. Being called a “fire crotch” was one of mine. What are some of yours? Once we can make peace with “all that,” and move along now, then we start attracting truly positive and uplifting people into our lives.

These are the people who become our lifelong friends and exude to match our newfound confidence, not shame.

As cheesy as I think self-affirmations can be, I also think it is entirely important to remember to smile and laugh life away sometimes. Seek out some deep belly chuckles. It will take the heaviness of the world right off of Atlas’ broad shoulders with one big, cheeky guffaw.

Take small moments every day to smile big, and make peace with anything grimace-inducing. Recipe number one for gaining confidence, sass, and a little newfangled pizazz starts with the ability to laugh at ourselves.

Elon Musk’s Twitter feed has been my recent go-to for humor of many varieties, ranging from blueberry muffins that look uncannily similar to Chihuahuas, to nerdy math humor that I don’t entirely understand yet but still appreciate. No matter what it is, just find something, somewhere, every day, that helps put the past to rest in peace. This opens us up to learn so many new things. I committed to playing the piano again and it has become one of the truest sources of pure joy in my life. I’d never have picked it up if I were still stuck.

9. Find hobbies outside of the relationship.

This is super, duper, exponentially important, especially if someday we are not with this person anymore, and everything we loved to do revolved around them.

Unfortunately, sometimes the shared hobbies are what bring two people together, in which case refer back to number eight. Playing the piano, knitting, reading, biking, ballet classes, kickboxing, language classes, any independent hobbies that take us outside and away from the relationship are wonderful outlets that can never have the joy sucked out of them, ever, by another person. That’s huge.

Nobody can ever take away from me the things that I enjoy doing just for the sake of myself.

That is liberation.

10. Remember, our only way out is through.

Love can’t save us from death, only dying can do that.

If we are careful, when we choose our love wisely, it will be all we feel when it is time for us both to finally let go. Living is tough enough sometimes without the added pressure of “finding the one.” Developing ourselves with time spent alone is a true blessing.

Singledom is not a curse. We can always remember that the best kind of love is simply the peaceful acceptance that we have for ourselves. Cultivating this type of appreciation and gratitude takes time. This is why it is so, so, so important to have patience with life (ahem, ourselves).

Don’t get too caught up in having it all “figured out,” or getting married to the first guy who buys us a ticket to Paris, or moving in with someone before having other investments. Choose wisely, and don’t be afraid to choose staying late for a report, or an extra hour after work for a yoga class, or a weekend getaway with girlfriends in the mountains.

Life begins and ends with, well, essentially the same thing. A fragile little body, beating and breathing. 

Conclusion: Date someone older, if only to see what it’s like.

…and move on if it doesn’t work out.

Never forget that we are always our own number one. At the end of all of our time here, we are often reflective and look back at our lives.

Let’s give ourselves the chance to see the people who didn’t stay as the people who guided us back to ourselves. We are always the leaders of our lives. So, whether we stay, or whether we walk away, there is so much more to love than staying in the wrong spot, waiting for someone else to make us feel all right.

Only we can do that.


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