11 Ways Of Flirting With Older Women

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A woman ages like fine wine, they say. Perhaps, that explains the mysterious pull that most young men feel toward older women. If you’re one of them, you’re likely wondering about how to deal with such a crush. How should you go about flirting with older women without coming across as a creep or being offensive? And what are some flirty questions to ask an older woman that won’t make her cringe?

It’s important to address these questions if you don’t want to end up on her block list. Answers are what we’re here to offer. In this article, we outline 11 tips on how to flirt with older women effectively, backed by actionable and helpful suggestions from psychologist Nandita Rambhia (MSc, Psychology), who specializes in CBT, REBT, and couples counseling. Read on to find out how to hit on an older woman with grace.

How To Flirt With Older Women — 11 Ways To Make It Look Effortless

Table of Contents

So, how often do younger men flirt with older women? Well, if we go by the recent trends in age-gap relationships, the older woman-younger man dynamic seems to be getting quite popular. This Reddit user’s experience gives an interesting insight into why that is. He says, “Yes. Had many flings and dated older women in their mid/late 20’s and early/mid 30’s when I was 18/19 and early twenties. They taught me a lot and taught me how to please a woman and communicate. I loved it. Fond memories.”

Clearly, younger men are drawn to older women for a reason. But do older women like younger men? Well, don’t fret. Older women may have seen a few more summers than you, but that doesn’t mean they’re out of your reach, young man! All you need is to play your cards right and that involves learning how to flirt with older women tastefully. To help you with that, we have listed 11 helpful suggestions on how to talk to older women effortlessly:

Related Reading: Dating An Older Woman: Benefits, Challenges, and Tips To Make It Work

1. Flirt with confidence

If you’re wondering how to tell an older woman you want her, confidence is your biggest ally. Nandita says, “Young men need to look and feel genuinely confident about themselves.” She also shares a few actionable tips on flirting with confidence to catch the attention of older women:

Don’t be nervous. Practice deep breathing to calm your nerves
Don’t be hesitant to ask questions or state your opinions. It reflects a lack of self-assuredness and impedes your ability to make a great impression
Actively listen to her points of view and continue the conversation accordingly

flirty questions to ask an older woman — You should be confident while flirting with an older woman

My friend, Anita, who’s a 45-year-old professor, started a steamy romance with a young intern in his 20s a few months back, and they’re still together. When I asked her what attracted her to him, she explained, “I loved his confidence and the way he didn’t even make me feel the age gap when we interacted.”

2. Maintain eye contact

Steady eye contact is a must when you’re trying to woo attractive older women, or any woman, for that matter. It’s an impactful way of non-verbal flirting. It shows you have a genuine interest in her and that you’re confident and self-assured. Nandita advises, “Look at her while talking, but don’t stare at her, as that might make her uncomfortable. Learn to balance eye contact.”

This is what attracted Bella, a coworker of mine, to her gym trainer, who was 10 years younger than her. In her late 30s now, Bella loved the way her 28-year-old gym trainer made eye contact with her every time he helped her with a workout. The fun began when Bella stared back at him, hinting that she liked what he did. Soon, he asked her out, and they have been dating for a few months now.

Related Reading: Older Women Dating – My Office Romance With A Younger Man

3. Smile seductively

Wondering how to tell an older woman you want her? Here is the secret to mature flirting—smile seductively. Try it and you will never struggle in your attempts to woo an older woman. A genuine but loaded smile is among the things that attract a woman to a man. Nandita says, “Smile while having a conversation or interacting. Smiling seductively can be a great way to initiate an intimate or special bond between the two of you. And if you’re lucky, you’ll surely see signs an older woman wants you.”

4. Compliment her

Verbal flirting is the answer if you’re wondering how to chat up attractive older women with ease. On that front, nothing beats the effectiveness of genuine, heartfelt compliments. Nandita warns, “But compliments shouldn’t extend to flattery.” She adds a few tips on how to compliment an older woman:

Make sure your compliments are sincere and genuine
Refrain from generic compliments such as “You look so pretty today!”
Specific compliments, such as “I simply love the way you laugh”, “I appreciate how you’ve achieved all your life goals by 40”, or “I love the way you’ve styled your hair” work wonders

how to flirt with older women — Never mention the age difference when flirting with an older woman

5. Avoid talking about the age difference

Yes, you both know there’s an age difference between you but don’t always focus on that. Age is just a number when you both have a genuine interest in each other. For my friend, Rhea, the sense of connection she felt with her younger partner far outweighed any concerns about the age gap.

She feels rejuvenated and more alive than I’ve seen her in a long time, and that’s because they don’t navigate their relationship through the prism of societal norms and expectations surrounding the age gap between romantic partners. Nandita agrees, and shared the following tips on how not to let the age difference loom large over a potential connection:

Talk about the age gap only if she’s comfortable talking about it
Even if you’re talking about it, you can just slip in a word or two
Don’t emphasize too much on the age factor, as that shouldn’t be an issue if the two of you are comfortable with each other and enjoy each other’s company

Related Reading: 15 Reasons Young Men Fall For Older Women

6. Flirt with respect

When trying to figure out how to talk to older women, remember there is no alternative to respect. Respect and healthy boundaries go a long way in ensuring you don’t cause offense or come on too strong when you flirt with older women. Remember, an older woman has more life experience than you, and her sensibilities may be more evolved or simply different than yours. So, it’s vital to tread lightly. Nandita offers the following tips on mature flirting that can help you prevent getting off on the wrong foot:

Be subtle in your flirting overtures at the beginning. You can gradually build up the intensity if she responds favorably
Avoid crude and vulgar words, there is nothing cool about it
Avoid below-the-belt humor

7. Talk about interesting topics and current events

Most older women love meaningful and deep conversations and are drawn to men who can hold their own when talking about complex issues and are abreast with the goings on in the world. If you’ve been crushing hard on an older woman and want to sweep her off her feet, this mature flirting technique will stand you in good stead.

Nandita says, “It’s important for younger men to showcase their knowledge on various topics and talk passionately, be it about sports, politics, or music.” Also learn to actively listen to what older women have to say, to pick up cues on what to talk about next. Sure, this may take some effort on your part but if you’re genuinely interested in the older woman you’re pursuing, it will be well worth the effort.

8. Infuse humor

A great sense of humor never fails to impress women. It especially works wonders when you interact with older women. Nandita says, “The humor needs to be classy, not lame or crass. One has to be ready with witty comebacks.” So, let that witty side of yours shine through if you want to see signs an older woman wants you. At the same time, don’t try too hard to be funny. Make sure your humor is organic and contextual.

how to talk to older women — Older women love chivalry

9. Be chivalrous

Chivalry is often considered an old-fashioned quality and is becoming extremely rare these days. Nonetheless, many older women appreciate it. If you want to be seen as a potential romantic interest, it’s time to brush up on those gentlemanly qualities. Nandita offers some tips on mature flirting with attractive older women:

Open the car door before she gets in
Bring her flowers
Walk or drive her home after a date
Be polite, not just with her but also with other people around you
Make a move with subtle touches, such as a brush of the arm, to see how she responds and whether she’s in her comfort zone

Related Reading: I Am Attracted To A Younger Man Who Is The Opposite Of My Husband

Ashley, a single mom from California, who is in a relationship with a man 8 years younger than her says, “He brought me flowers on the first date, got up to greet me when I walked in, and held the door for me as we were leaving. Who does that these days? I was quite taken with him after that.”

10. Maintain texting etiquette

While flirting through texts is commonplace these days, you need to make sure your dating texting etiquette is on point. One of the most prominent rules of flirting with older women that Nandita talks about is avoiding slang and abbreviations in texts. Also, not prodding her about her past relationships.

She says, “As an older woman who is probably not from your generation, she probably wouldn’t be in tune with the latest lingo. This is just an effect of a prominent generation gap. So, if you’re wondering how to hit on an older woman via texts, avoid jargon and slang that she may not be used to.”

11. Don’t be too clingy

One of the golden rules while flirting with older women is not to be overbearing. Nandita advises, “Be independent. Initiate texts and calls. But don’t overdo it.” Being clingy will not go down well. An older woman is mature and independent, and she’d expect some amount of maturity from you too.

Frequently Asked Question

1. How do older women flirt?

Now that you know how to flirt with older women, let’s look at how older women flirt. Well, most older women often flirt subtly. They will not go all out to gain your attention but will flirt with their eyes or smile. They may also send you mildly suggestive texts to flirt subtly.

Infographic On Signs An Older Woman Wants You

So, now that you’ve mastered the art of flirting with older women, how can you be sure that an older lady actually craves your company? And how do you make sure you’re not misreading the signs? Let’s look at the list of signs that an older woman wants you:

Final Thoughts

Older women are perhaps the eternal elixir for younger men. Be it teenagers or men in their mid-20s or mid-30s, it seems older women seem attractive to most men because of their worldly ways, life experience, and charm. And such age-gap relationships are becoming quite common. Do older women like younger men? Well, they surely do when the man approaches them with confidence and respect.

But when it comes to flirting with older women, most men are hesitant and scared that they might end up offending them or messing things up. They also often have no clue about the flirty questions one should ask an older woman. So, we hope, with the 11 tips to flirt with older women that we’ve shared in this article, you will have a field time impressing some beautiful and graceful lady someday soon. We wish you all the luck!