If you’re looking to pickup cougars, milfs, and other older women, then you should try and break the ice with these must-use methods. I promise, they will work well! Give one or a few a try and see what happens. Chances are, you’ll end up in bed with a mature woman because eventually, one will take the bait!
“They say fine wine gets better with age—clearly, they were talking about you.”
Does something like that work on a person? You bet it does.
I talk to a lot of other guys about picking up women, and a lot of men I run into really have a thing for the older, experienced lady. Believe me, I love cougars, I appreciate older, elegant women, and I’m telling you, 100%, that these little, fun lines will get her swooning, especially when you add a bit of macho charm. The number of times I’ve gotten laid by older women due to using pickup lines is crazy.
Here, I’m going to share some of my favorite pick up lines that work on older women, and give you some general tips on what has worked for me. Before you know it, you will have her begging to come home with you, and you may not even have to ask.
How Effective are Pickup Lines for MILFs?
You will be surprised by how effective a pickup line can be when you start using them on someone. My best advice when trying to pick up an older woman is to respect her, show a lot of interest, have some wit and playful banter, and of course, she’s going to want a guy who is confident.
Many of these women are looking for the perfect excuse to get in bed with a younger man, so keep that in mind. Classic pick up lines may not work on these women, who also often live a life of elegance and want to be in sophisticated conversation. She will want to feel like your world is totally focused on her during the interaction, and she will want it to be genuine.
Pay attention to how she acts as you work hard on your connection, and you are going to have to read her body language to decide which of the following pickup lines will work best. I’ve laid them out based on categories like Funny, Smooth, Cheesy, and Flirty…and of course, Dirty. (You would be really surprised to see how well these work!)
My Best Pick Up Lines for Mature Women
Like I said, I have been using pickup lines on women for years, and since I love dating older women, I feel like I’m one of the best guys to share this info. Before I get into this, though, I have one word of caution: keep it classy, and always assess the situation before you start spilling pickup lines. If she’s not interested, she’s not interested. Move on.
Funny Pick Up Lines
Whether it’s older or younger women, they simply love humor. So landing a funny pick up line can always be effective.
Here are some examples:
- “Did it just get awkward in here, or did I just imagine our wedding on sight?”
- “I’ve discovered a secret location perfect for two. The only catch? You have to say yes to find out.”
- “Let’s exchange numbers and see who regrets it first. Just kidding. I won’t.”
- “I believe in love at first sight. Did you just fall in love? I did.”
- “My jaw didn’t drop. It just… respectfully fell in admiration.”
- “You must do hypnosis on the side, because whenever I look your way, I zone out.”
- “Do you have a map? I just got lost in your eyes.”
- “If we’re rating things, you just broke the scale. Now what?”
- “Quick question: Do you mind if I put you in my phone under ‘plot twist’?”
- “If we went to the movies, I’d be too busy watching you to follow the plot.”
- “I’m new around here. Know any places with strong drinks and stronger chances of bumping into you again?”
Smooth Pick Up Lines
Humor can be a great way to impress and pickup a hot older lady, but it’s not everything, and sometimes you need to be a bit more smooth and a lot less funny. Here’s some of my best smooth pickup lines.
Practice these in the mirror, and definitely memorize these so that they are right there when you need them.
- “I expected wisdom to come with the years… but no one warned me about jaw-dropping gorgeous too.”
- “I swear I’ve seen you somewhere before—were you in my dreams or just every ‘90s magazine ad I loved?”
- “You look too familiar to be a stranger. Let’s fix that either way.”
- “I say we gamble on the night—you pick who wins, and we both go home happy.”
- “You’re definitely in my top two most beautiful women I’ve ever seen… and the other one was just my reflection in a funhouse mirror.”
- “I thought I liked this place—then you walked in and upgraded the whole experience.”
- “Wanna play ‘guess my age’? Loser buys the drinks. Winner gets bragging rights and possibly a second date.”
- “I’m torn between ordering a cocktail… or just asking what someone like you recommends.”
- “You clearly mastered looking incredible. Got any other talents I should know about?”
- “Something about you is making my instincts throw a parade right now.”
- “Let’s snap a photo—I have a feeling this is one of those stories we’ll want proof of later.”
Cheesy Pick Up Lines
If you need a great icebreaker, consider a cheesy pickup line. These often work best when your target lady is with her friends at the bar or you are sure that she’s going to like a little bit of stupid, lighthearted conversation. If she laughs at these cheesy pick up lines, your chances of hooking up are much higher.
- “So… should I keep calling you ‘Gorgeous,’ or are you ready to give me your real name?”
- “Are you some kind of mythological miracle? Because I’ve been wishing for you without even knowing it.”
- “Are you secretly a lens filter? Because everything looks better when you’re around.”
- “Even with 20/20 vision, it’s crystal clear—we’re meant to be.”
- “Need a breather? You’ve been sprinting laps in my head since you walked in.”
- “Be honest—how often do you say yes to ridiculously charming strangers?”
- “Quick—can I grab a photo with you? I need to prove to Santa Claus that I’ve already found the perfect gift.”
- “Are you part of tonight’s show? Because something definitely just lit up the room.”
- “Not to start drama, but your arrival may have just caused a jealousy emergency.”
- “I had the smoothest opening line planned… and then you showed up and short-circuited my brain.”
- “Excuse me, but we’re going to need backup—your looks just caused a public swooning incident.”
Flirty Pick Up Lines
Older women tend to love bold guys, and you don’t need to waste time on a lot of small talk when you just go in and start flirting. Here are some of my favorite flirty pickup lines:
- “Do you go by your name, or should I just call you the highlight of my night?”
- “Would it be weird if I stared for a second longer? This feels like a scene I’ll want to remember forever.”
- “I don’t know what’s brighter—these lights or your eyes. Actually, never mind, I do.”
- “You’ve got that rare talent—making style look effortless no matter what you wear.”
- “Who gave your eyes permission to outshine constellations like that?”
- “You walk in and suddenly the whole place has a vintage Hollywood vibe.”
- “They say true beauty blossoms with time… and looking at you, I believe it.”
- “Somehow, you’ve managed to outshine women half your age—and they know it too.”
- “Is this timeless beauty something you were born with, or is it just your natural glow leveling up?”
- “Do people always look at you like that, or am I just the latest victim of your charm?”
- “A night like this deserves elegance—and lucky for us, you brought it. Mind if I tag along?”
- “You look really good after your run. You know, you’ve been running through my mind all night.”
Dirty Pick Up Lines
When the mood is right, a dirty pick up line can work almost every time. Mature women are experienced, and if she seems receptive, try these dirty pickup lines:
“You cover the check, and I’ll cover dessert—at my place.”
“This date’s been hot… ready to turn up the heat somewhere a little more private?”
“If you look that good dressed, I’m officially dying of curiosity about the undressed version.”
“Either your eyes are magnetic, or they’ve already removed half my clothes.”
“Did I catch you picturing me naked, or am I just projecting?”
“You might want to remember my name— you will be screaming it later.”
“That outfit’s a masterpiece—but I think I’d look even better tangled up in it.”
“What’s your coffee order? Just want to be fully prepared when I’m making it at your place in the morning.”
“I specialize in body mapping—care to be my next… highly detailed subject?”
“You look like you could teach a masterclass in cardio. How about a hands-on lesson?”
Making the Best Pick Up Lines Possible
If my pickup lines aren’t your thing, no problem. I can help you make your own, too. Here are some great tips of mine that you can use:
Always Compliment Her
Older women know they look good, and they also love hearing about how good they look. Always compliment her looks, but do it in a genuinely sincere way.
Whatever You Say, Say it With Confidence
The pickup line is only part of it. If you have confidence, you can say almost anything, and you will have her falling right into your arms.
Be Respectful
Older women demand respect, and if you take this approach when picking her up, I predict she will be in your bed in the very near future.
Now that you know how to impress and older woman, get your guys together and go out and create a spark. Be direct, and don’t forget to be charming, respectful, and fun.
Conclusion
Well, that’s all you need to know about picking up hot older women through the use of pickup lines. If you’re man enough to give them a try then you shall reap the rewards of doing so. Find out how well they work by giving them a try yourself! But first, read my official Milfplay review today!