How to Make an Older Woman Fall in Love with You

make older woman fall in love

All younger guys, at some point, fantasize about having a relationship with an older woman. But how exactly do you bring the cougar to your door?

The Graduate, Sex and the City, Cougar Town, Desperate Housewives–all popular movies and TV shows principally revolving around the subject of older women dating younger men.

This phenomenon has an almost ubiquitous presence in modern media, and, despite the whole issue of chickens and eggs and which came first, the same phenomenon seems to have spilled out onto the streets of reality. So much so that it’s not only acceptable for a younger guy to date an older woman now; it’s actually quite desirable.

Ever the twain shall meet!

It doesn’t come solely down to popular media as to why this particular human pairing occurs so commonly. There are some fairly solid reasons as to why the older woman and younger man make such a good match.

Sexual and physiological factors are prime reasons. With men hitting their sexual peaks between the ages of 18 and 21, and women somewhere around their mid to late thirties, the conclusions to be drawn from this particular set of realities are obvious.

However, the free and more willing of the older women out there are vastly outnumbered by the quantity of young studs vying for their attention, giving them the pick of the litter. How can you compete against such overwhelming numbers? Read on for a few vital tips on the age-old art of seducing and securing the attentions of a cougar.

#1 Dress to impress. The average older woman has been around the block a few times. She’s seen more than you have, heard more than you have, and experienced more than you have. That also means that she’s experienced a much wider range of social situations than you, and she knows how to dress for each and every one of them. Moreover, she feels entirely comfortable doing so.

It is paramount, then, that you get the dress code right whenever you are in her presence. Making the mistake of wearing a t-shirt to a smart, casual event or a tuxedo to one that requires full morning suit attire is likely to leave her feeling distinctly underwhelmed.

Even worse, if a romantic connection has already been established, you could leave her feeling embarrassed in front of her peers–an end result that can, at best, lead to a frosty goodbye and a subsequent dismissal of your existence. Do your research, and try your best to be the man she knows she deserves. [Read: 13 steps to be the sexy guy you’ve always wanted to be]

#2 Stick your chin out. You’re a young guy, and that’s a major part of the attraction for older women. They like who you are–all that freshness and youthful spirit–and don’t want you to pretend to be anything else.

Irrespective of age, there are certain traits that women need to see in the male objects of their affections. You could be 18 or 80, but she still wants you to be a man–a confident alpha male with a keen eye and robust set of opinions.

Being a wallflower is not the way to a woman’s heart, and youthful indecision is more likely to turn her off than on. Be strong and show her that, despite your tender years, you know your own mind and are more than willing to share it. [Read: 10 ways to be manlier but not aggressive]

#3 Know when to keep mum. This particular caveat is almost the opposite of the previous one, and counsels you to keep your mouth shut on occasion. That’s not to say that you shouldn’t air your opinion from time to time. Not at all. She actually likes that.

What this point counsels is the importance of allowing free discussion on both sides. Some young men do try to dominate the conversation, but such a forceful and uninformed manner is unlikely to impress the independent and savvy older woman.

If you want to impress her, attempt conversation as a confident peer, but avoid commenting on subjects you know next to nothing about. She’ll identify your fraud in a second, and you’ll be lucky to get the time of day, nevermind her phone number!

#4 Avoid the obvious. Although she is an older woman and this rather apparent age gap lies between you, that doesn’t mean she that wants to be constantly reminded of the fact. Silly references to her being a MILF, cougar, or hot mom will not impress her, and will probably solicit the execution of a stingingly swift slap across the jaw.

If you want to charm her, talk about her apparel, her wit, her beauty–not how many wrinkles she has on her neck!

#5 Compliment her. The older woman is a lot smarter and keen-minded than the little air-heads of your own age group. But she isn’t so bitter and cynical that she doesn’t know how to appreciate the odd compliment.

In fact, as she as she passes through her middle years, she’s probably more receptive to her ever-dwindling supply of compliments than ever before. Make her glow with a few well-chosen words describing your appreciation for her, and watch her melt in your arms. [Read: How to compliment a girl and make her blush]

#6 Avoid flattery. There’s a huge difference between the act of paying a compliment and the act of attempting flattery. The former is a genuine attempt to express your appreciation for someone’s physical or cognitive attributes, and the latter, a form of deceit.

Don’t forget you’re dealing with an older woman, here. She’ll smell the BS in seconds and have you running for the hills, with your tail tucked firmly between your legs, if you offer anything less than the whole truth. You’ve been warned!

#7 Keep trim. Let’s be honest, here, one of the reasons you can get into cougar panties when your older counterparts have failed is your youthful vigor and physique. If you let yourself go and start getting a bit heavy around the edges, or short of breath at the briefest hint of a stiff walk, then you’re giving away your greatest weapon. If she wanted a conversation and a bill payer, she’d have stayed with her last husband.

#8 Location, location, location. At some point, you’re going to have to take her out on a date, which can be quite daunting, considering her experience in this field. Just remember: she’s no fluffy bunny, but a strong, confident woman who knows her own mind.

Take her to the kind of place a woman of her age deserves and expects–somewhere swish and impressive–and save the burger joints for the twenty-somethings. [Read: 7 date ideas men love but women actually hate]

#9 Games ain’t for dames. Similar to number nine, treat the woman with respect. Game playing is so far beneath her that it probably resides somewhere in the vicinity of the earth’s core. If you say you’re going to ring her on Tuesday, then ring her on Tuesday. Playing some kind of “treat them mean and keep them keen” routine is not going to work on this lady, and could backfire on you with spectacular effect.

#10 Give her air. As an older woman, she very much has her own life, and this needs to be respected. That late teen/twenty-something puppy love routine has no place in the life of a mature and independent woman of the world. Throwing yourself upon her at every possible juncture will make her feel stifled and craving the presence of less-demanding company.

[Read: 13 rules of etiquette for the modern gentleman]

Take advantage of our tips above to secure the cougar of your dreams. Who knows? It might just be a chronological mismatch made in heaven!

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David Cullen
David Cullen
David Cullen is frequently described as erudite, insightful and witty – but only by himself and only after several large glasses of Rioja....

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One thought on “How to Make an Older Woman Fall in Love with You”

  1. cougar says:

    I was 21 and she was 42 when we met. We were introduced when I interned at her company during one of my winter breaks from college. Right off the bat I found her very attractive and interesting and loved all of the chances I had to talk with her throughout the day. Our talk of films sparked my interest, as we are both huge cinema fans. I thought she was much younger (originally I guessed around 30) than her true age. I learned she was currently finishing a degree program as well, and on my last day at the company I asked her for her e-mail address so that we could “grab a drink together to celebrate our upcoming graduations.” I didn’t contact her until about six months later in the summer, and we had our celebratory drink the night before my 22nd birthday. I asked if she wanted to make this a date, and she expressed that she didn’t feel comfortable with that due to our age difference. I didn’t push for it, but asked if she wanted to go out again and keep things casual. She agreed and said that she enjoyed catching up with me. Fast forward a few weeks and two more “dates,” both of which ended with us making out in her car, and I visited her house for the first time. She lived alone, was divorced, and had no children. After several hours of discussing our pasts, what we were looking for in a partner, and setting boundaries with each other, we had sex until 4am and I spent the night. We began a relationship (kept secret from our families) shortly after and saw each other for the next year and two months. We had some of the best, and kinkiest, sex of our lives. You could cut the passion in the air with a knife when we were together based on how strong our feelings toward each other grew. Despite our original plans to remain unattached and keep things casual, we fell in love and shared things with each other that we never had with anyone else. Ultimately we found ourselves in different places in our lives and realized that there were some hurdles we were never going to clear. Eventually we made the difficult mutual decision to break up. The lines of communication are still open and we are still friends. We both agreed that we were open to trying things again in the future if mutual interest was still present and we are both single.

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