5 Dos and Don’ts For Picking Up Older Women
From hot mamas like Mrs. Robinson and Stifler’s mom to the quirky and bumbling Liz Lemon, older, attractive women, better known now as cougars, come in all shapes and sizes.
Micaela Schäfer for her new club tour. Gifs, screenshots and video are here
Micaela Schäfer is a German model, reality TV Star, DJane
Micaela Schäfer by Jorg Otto for Playboy Czech (May 2017)
Micaela Schäfer is a model, reality television star, dJane from Germany
Only in the past few years, however, have they’ve gained widespread popularity and acceptance. Though it seems moot now with her impending divorce, when Demi Moore married Ashton Kutcher in 2003, it gave older women hope that they could snag a good-looking, successful younger man without being scrutinized.
That being said, here are 5 things you should and shouldn’t say when flirting with an older lady.
5 things you SHOULD say:
5. So what do you think about… – The straightforward approach is more often than not the safest route to go. If you try to get elaborate when you try to pick up an older lady, then she’ll see right through it and you’ll end up nowhere.
If you’re sitting next to a cougar at a bar and you’re interested, carefully pay attention to what she’s talking about with her friends and/or the bartender and use that knowledge to make a move.
For example, asking her opinion about something shows that you’re into her, but in a non-invasive way, which will lead to more conversation…assuming she’s interested.
4. That’s a nice (insert accessory she’s rockin’) you have, where did you get it? – Fellas, asking about a woman’s accessory shows that you have an attention to detail and in a way, shows that you knowledgeable beyond typical guy topics. If you ask about an accessory (handbag is the best option), then the cougar will answer since there’s probably a good reason she decided to wear it out.
3. How’s it going? – It be a bit basic and seems boring, but if you’re trying to pick up a cougar at a bar or party, then this is a pretty easy conversation starter.
Before you approach the woman of your interest, you need to feel her out by paying attention to her body language. Whether or not she’s chipper or dour will effect your approach.
If she looks like she’s in a bad mood or bored, approach with caution, yet be upbeat because she may seem like she’s irritated when in reality, she’s just trying to find someone to talk to. Contrarily, if she seems like she’s having a good time, you need to be careful since you don’t want to interrupt her and get blown off.
At the same time, when you do approach her, do so with confidence because she’ll be able to snuff out false bravado in a heartbeat.
2. What are you drinking? – If you are at a bar, which is assumed, this is the way to go. This is especially encouraged if she’s alone and sitting at the bar. When a cougar is at a bar, she generally isn’t there to enjoy the atmosphere. As has been with personal experience, if you’re able to maneuver towards the cougar and she’s drinking, then it’s an easy way to strike up conversation.
1. Can I get you a drink? – This elaborates on the previous item, but it’s simple and to the point. Asking a cougar what she’s drinking is an easy way to open a conversation. Depending on how she answers this question, you’ll know exactly whether or not to move forward in the conversation. If she blows you off, then well, onto the next.
And here are 5 things you SHOULD NEVER say:
5. You look so young; I’m surprised you don’t have any wrinkles. – Generally it isn’t a good idea comment to mention age at all, especially if you’re trying to pick up a cougar. It doesn’t matter if you’re trying to be flattering by comparing her to an older celebrity or calling her Queen Elizabeth, if you don’t want a one way ticket to rejectionville, then don’t talk about ages.
4. You bear a striking resemblance to Liz Lemon. – You may think you’re being funny since the main character of 30 Rock is quirky and goofy, but to some, you’re saying they’re homely and hopeless in the field of love. Never ever say this under any circumstance — trust me, I’ve gotten into trouble for it.
3. Is that old or vintage? – Be careful to how you phrase a compliment because by calling something that a cougar has (whether it be an accessory or something she’s wearing) either of these terms, you’re inadvertently calling her old. Not only is it a tad disrespectful, but will make you look like an asshole.
2. That’s something my mom would do – We all love our mothers, but unless you have some weird Oedipus complex, you don’t want to sleep with her. Not only is that weird, but again, it is insulting the age of the cougar, even if she’s a couple of years older than you. You don’t want a mother, you want a lover. By bringing mom into the picture, that’s a quick conversation killer.
1. Anything sophomoric or would have been cool when you were in college – If you use a pickup line or move that you did in college, then kiss your chances of picking up a cougar goodbye. What they’re looking for (generally) is to strike up pleasant conversation, think of it sort of like a job interview.
The difference here is instead of landing a high paying job; the reward in this case is getting laid. Using sophomoric, cheesy pickup lines will most likely land you back in your seat and most likely embarrassed by your lame pickup attempt.