How to Charm a Lady Older Than You

How to Charm a Lady Older Than You

So you want to impress an older lady? You’re one of the millions of guys in your situation. If you don’t know anything about flirting with older women, don’t worry. Most younger guys don’t because they believe things they see in movies and TV shows. Life isn’t a movie. Mature women aren’t all the same. And even though you should show the same traits online and offline, your approach should be different on dating sites and bars. We’ll start with online dating because that’s how most MILFs find partners nowadays.


Online dating is part of modern culture, and everyone seeking dates has at least tried to find them online. Everybody knows about mainstream apps, but they aren’t the best solution for younger guys who want a MILF date with older ladies. Niche sites are a much better choice because only those mature women who want to meet younger men join the platform made for MILF dating. Older women on general sites usually want guys their age. On the MILF dating site, guys their age have 0 chance. But younger guys are a hot topic there. However, don’t expect to register and pick women like apples. You still need to know how to charm them.

When it comes to exploring no strings attached relationships and finding potential partners for one-night stands, specialized platforms are tailored to cater to such preferences. The best dating apps for casual dating and one night stands provide a convenient and discreet way for individuals seeking short-term connections without the commitment of a long-term relationship.

Be Proactive and Initiate Conversations

Older women fall for confident younger guys who aren’t scared to approach them. And it’s much simpler to start a conversation online than in person. Reading profiles of women you’d love to meet gives nuggets you can use to come up with ice-breakers. Not only that, but you can think of conversation topics based on the info you find on their profile. But be careful; a bottomless pit called overthinking swallows many men. Don’t think about every message for 10 minutes before sending it. The conversation on the chat should feel like a conversation in person.

Don’t Brag Too Much!

If anything is sure in this life, MILFs hate younger guys who can’t stop bragging. Remember that a lion doesn’t have to say he’s a lion. Guys who brag all the time are overcompensating for something. If women can’t find what exactly they’re trying to make up for, they always assume the problem is, how to say this, under their belly buttons.

Less is more when it comes to flirting with MILFs. Also, guys who keep moving the focus on a conversation back to them never show interest in the women they talk to. How could they when they can’t stop talking about themselves? So remember, it’s not about you; it’s about them.

Make Decent Compliments

Compliments are crucial, but not like most men think they are. You aren’t an action hero from a movie, and MILFs aren’t supervillains, so you have to shoot 198079 bullets to defeat them. Picking your shots will make a lot more impact. If you just put them under the avalanche of compliments, they’ll think something is wrong with you. And don’t make desperate compliments about their curves or other things boys in puberty would say.

Don’t show that weakness online, and you’ll start getting more dates immediately. Thank us later, but first, read tips for seducing MILFs offline.


Flitting offline is a different beast than flirting online. It’s easier to get results online because it’s easier to hide how nervous you are. You also have enough time to think about what to say. But a good thing is that you can transfer skills you hone online into the offline world and start getting more dates in bars. However, some factors of offline dating are irrelevant online, but you can’t neglect them when meeting in person.

Know the Manners

Hot older women don’t like savages who don’t know how to behave in the civilized world. Guys who pick on waiters, eat with their hands, or never hold doors for them usually don’t get second dates. Women want to be with guys who won’t make them ashamed everywhere they go.

Dress Smart

How you dress is your thing, but if you want to seduce older women, you may have to rethink your fashion choices. You don’t have to spend every second in a three-piece suit, but don’t walk around dressed like a hobo because they’ll move on to the guy who takes care of his appearance.

Show Spontaneity

Movies are wrong about many things, but they never fail to show that spontaneity is hot. Especially to MILFs who want dates with younger guys because men their age are too boring for them. So if you’re trying to impress a MILF in person, don’t play it safe. Show you’re willing to take calculated risks (women love that) and suggest spontaneous activities every now and then.

Be a Good Listener

Older women love men with good listening skills because having a conversation with someone who actually wants to hear your words helps deal with stress and anxiety. Even if you’re talking about something completely irrelevant, don’t stop listening. Many doors open to those who pay attention. Never forget that.

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