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Younger Women Gushing Over Older Guys – Advice for the Millennial Female

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At the age of 24, I worked the night shift at a very popular Atlanta restaurant. I encountered a number of older gentlemen who seemed to have the hots for younger women. Besides the creepy 60 year olds with submissive wives and spoiled teenage children, there’s a group of wandering souls who fell a bit closer to me in age. I call this “The Feasible Group”. The Feasible Group consists of average to very attractive men between the ages of 26-35. There was once a 38 year-old who snuck into the Feasible Group but honestly he looked just over 30. But besides him, the men who I categorize as feasible are older and normally well established. In laymen’s terms, they’re financially stable. For instance: they may have one more degree than you do, or just one more means of transportation. They may have more mula saved in their bank account and could possibly own their own home. As both men and women increase in age, they often render more accomplishments. And although my personal preference in relation to older men is between 26 – 35, you may enjoy gentlemen who fall between 28 – 37, 38 – 45, or whichever older age group you deem physically appeasing and still socially appropriate.

You see, we’re not referring to Sponsors and Sugar Daddies. That’s another post for another time. This article strategically focuses on dating a seemingly more accomplished person than yourself, that might be a few years older than your last boy toy.


For example: I dated a 29 year old with a stable job, a steady income, no roommates and a one bedroom apartment. He drove a nice car, was attaining his Master’s Degree, and in constant search of bettering his career and increasing his income. I even admired his decision to have each of his bills drafted from his account automatically. It can be argued that I’m fairly easy to please, but there are a few personal characteristics this gentleman had that most men do not. He was financially savvy and possessed a desire to succeed. He had goals and never seemed complacent. He was eager to grow and learn and invest in his future. Okay okay, I’m hopping off now. But while he was practicing adult-like behavior let’s just say my sh*t was not together.

Without exposing too much about my inability to ween completely off the support of my parents, I realized from our first conversation there were things I needed to work on before I considered us “compatible”.

But due to my lack of current financial and professional attributes, was I forced to pass up the opportunity of dating what appeared to be a pretty decent dude? Heck no! So what’s a girl to do when their crush is looking for a life mate, a soul partner… and you’re falling just a little short? You pay attention to these 8 points. Thank me later.

  1. Be Upfront – Don’t Flex

After gaining a good sense of your possible partner’s assets and agreeable qualities, be forward and direct about your current “situation”, whatever your situation may be. If you still live with your parents, say that. But make a point to add that you’re saving money to move out. Maybe you want to invest in property; purchase your first home or condo. Just make sure you tell the truth. Never lie about major (or minor) details – it’ll all come to light.

  1. Sell Yourself

No, not like a prostitute silly. Just paint the best picture of you. Highlight your gifts and assets, force him/her to pay strong attention to your positive qualities. If you’re a hard worker with a college degree, talk about your interest in learning and desire to better yourself. If you’re not the neatest person in the world, stray away from inviting him over. Remember, they might run into day old dishes or that laundry basket you left sitting in the hallway. Present your best self first, they’ll get the rest of you later.

  1. Be Confident

Be confident in your worth and know your standards. Don’t even think about dimming your light or making yourself seem small! Be as bold and big as you imagine yourself to be. Make them feel lucky to even have caught your attention, let alone coax you into a date. Sure he’s super cute with the whole world in front of him, but none of that matters without a bomb ass chick like you on his side! Huah!


  1. Be Ambitious

Own up to your dreams in conversation. Talk excessively about your goals and wishes and how you plan to achieve each of them. Keep busy. Continue to fill your schedule with professional engagements that help propel your career. Never place your bae of choice before scheduled events. Prioritize your time keeping your ambitions at the forefront.

  1. Take Care of Yourself

Don’t come off as the needy partner… too soon. Present yourself as an independent woman willing and ready to provide for yourself. Take care of the bills you do have and display a super sense of adulthood. If he’s offering to help with a few things, be accepting. But allow him to acknowledge your strong work ethic first. Let him see the potential in your future and your yearning for a reputable career and stable income. Be about your sh*t, and don’t look for handouts. They want a partner that’s relatable: able to split emotional and financial responsibilities right down the middle. No matter how bad you’re struggling, keep it together. There’ll come a time when you’ll need something, and he’ll be right there for it. Just fake it until you make it… just for a little while longer (But if you’re faking it too much, re-read step number one).


6. Pick Up The Tab

Once again, let me restate the fact that I love being spoiled. But nothing turns a man on more than a woman who can switch around societal roles. Treat your guy to a dinner or two. Pick up the tab every now and then. Allow them to understand that if you had it, he’d have it too. This  allows him to become even more comfortable with spending, sponsoring, and spoiling. He now understands that any money he drops on you, you would willingly do the same for him – if you could. Once he’s convinced he’s not being used by a woman he desires, he’ll then choose to display an equal form of appreciation, reciprocating the attention you’ve shown him.

7.   Never Let ‘Em See You Sweat

Never let the guy of your dreams see you at your worst. Not yet anyway. Soon enough he’ll catch you on your off day: rollers and a head scarf, decked out in a onesie pajamas set. Don’t forget about those drunken nights when you’ll call his phone twenty times for some physical attention. Let’s just keep the crazy under wraps for now. Look presentable, better yet bomb, and remind him of why you caught his attention in the first place.

  1. Last But Not Least, Express Yourself!

One quality that’s considerably mature is the ability to express your feelings throughout the relationship. Speak up for yourself! Discuss what you like, what you don’t like, how you feel, and how things could be better. Elevate the topic of conversation by delving into each of your emotional realms. Constantly expressing where each of you stand and how you see the relationship evolving is key. Just because he’s older doesn’t mean he has to gain control and stay there. Take charge of your emotional world! Let him know who he’s dealing with! Remind him that age is honestly just a number.

Annsleigh Denise is a graduate of Spelman College, earning a Bachelor's Degree in English and a Minor in Multi-Media and Professional Writing. She is a multifaceted creative, focused on the inner-workings of print, publication, and Broadcast Journalism. Possessing notable editorial skills, Annsleigh aspires to utilize her professional experience to impact the world of media.

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