~ archived since 2018 ~
Popular
Other
[deleted]
[–]vroomvroomski 98 points99 points100 points 4 years ago (3 children) | Copy Link
Zach Wilson burner account
[–]sublimeonskunk 9 points10 points11 points 4 years ago (0 children) | Copy Link
Rofl
[–]HootingMandrill 3 points4 points5 points 4 years ago (0 children) | Copy Link
As if he'd need advice, man knows what he's doing.
[–]what_it_do_bby 2 points3 points4 points 4 years ago (0 children) | Copy Link
🤣🤣🤣
[–]focus_flow69 133 points134 points135 points 4 years ago (8 children) | Copy Link
Be fun, have fun.
Joke around, tease, flirt, banter.
Ask lots of questions. Ask daring questions. Be curious.
Be polite and a gentleman. Be respectful but also don't be afraid to be bold.
Eye fuck the shit out of her. Stare at her body if she's dressed up and if she catches you just have a shit eating grin and don't acknowledge it. If she calls you out, just say my apologies, im easily distracted 😏.
Older women want to feel desired, so do things that will make her feel that way.
[–]LolaBijou 19 points20 points21 points 4 years ago (0 children) | Copy Link
Add compliment her, but genuinely. And be confident, dress well, and smell nice. As a woman, I agree this is all good advice.
[–]punittt 61 points62 points63 points 4 years ago (3 children) | Copy Link
Eye fuck the shit out of her lololol
[–]iiexistenzeii 18 points19 points20 points 4 years ago (1 child) | Copy Link
I mean... If the vibe is right, go for it.
The above comment is on point 99% except the eye fucking bit XD
[–]punittt 6 points7 points8 points 4 years ago (0 children) | Copy Link
Yeah I agree, it was just funny the way they phrased it
[–]VivaIlSesso 3 points4 points5 points 4 years ago (0 children) | Copy Link
I did that to an older woman and it worked lol
[–]crackers-do-matter 1 point2 points3 points 4 years ago (1 child) | Copy Link
Hey, what would you say be daring questions? I've always had hard time asking such things.
[–]focus_flow69 2 points3 points4 points 4 years ago (0 children) | Copy Link
Would you rather be poor and hot? Or ugly and rich? Why? Tease her whatever the answer is.
Are you the same person at work VS on a date? Which one do you enjoy more? Do you feel pressured to wear different hats? What's life like for you? Learn about her life and offer your opinion. Compare and contrast your lives.
What do you think about fuckboy culture? How was dating for you growing up? When did you lose your virginity? Were you more sexual younger or older? What's your type? Tease, make assumptions, be judgment free and share dating/relationship/sex stories of your own. Don't act too thirsty when talking about sex. Be calm and very matter of fact like it's no big deal. Since it is no big deal.
Any creepy guys try to pick you up recently? Or any hot guys you've picked up? Any funny stories? Talk about seduction and how clueless you once were or other people can be with dating. Bond and laugh over shitty dating app stories. Share your own stories.
Literally any question can be daring if you make it so. Daring questions for me are just questions or subjects most people would be too scared to bring up or think it's too tabboo or personal to talk about with someone you don't know well. If you ask them, bring it up and share your own opinion and experiences with it, you normalize the tabboo/perosnal questions and shows you are comfortable with whatever. It's almost like a cheat code in Mario where you use the flute to warp to level 8. By asking these questions that normally only close friends would ask, you instantly jump the line to that level.
If they ever react poorly to a question or act surprised you asked, just apologize and say you are an open book and like to ask and talk about anything, then move on. When you ask daring questions, you risk a poor reaction or a moment of rejection. But it makes for much more exciting conversation and shows confidence. It also works for me because my personality is to not give a fuck. I will ask and do what I want. Life's more exciting this way and way too short to ask boring shit.
[–]4goodluck -1 points0 points1 point 4 years ago (0 children) | Copy Link
so do married women…proceed w caution
[–]Segundaleydenewtonnn 25 points26 points27 points 4 years ago (0 children) | Copy Link
Just have fun. No games or psychological tricks. Older women have no time for bullshit. Go for what you want with confidence
[–]grindforthegold 57 points58 points59 points 4 years ago (1 child) | Copy Link
is it your boys mom?
[–]sublimeonskunk 7 points8 points9 points 4 years ago (0 children) | Copy Link
I just saw a video about this. It had a happy ending.
[–]ikeepon 59 points60 points61 points 4 years ago (3 children) | Copy Link
She’s probably DTF as long as you don’t f*ck it up.
[–]Dakessian 3 points4 points5 points 4 years ago (0 children) | Copy Link
Yea I was about to say.
[–]getmeb 0 points1 point2 points 4 years ago (1 child) | Copy Link
What is DTF?
[–][deleted] 4 years ago (6 children) | Copy Link
[permanently deleted]
[–]kellykebab 4 points5 points6 points 4 years ago (5 children) | Copy Link
Probably he caught feels and the lady wasn't having it.
These older chicks are going to be vastly more experienced, more jaded, more particular about what they want, better at manipulating men, and have higher expectations to boot.
Boggles my mind that any young guy is interested in that kind of woman.
[–]Pedadinga 11 points12 points13 points 4 years ago (1 child) | Copy Link
I agree, but instead of jaded I would say not willing to put up with bullshit, and we’re actually LESS likely to manipulate men. We don’t have time for that shit.
[–]kellykebab 0 points1 point2 points 4 years ago (0 children) | Copy Link
Mmmm. Based on my experience, maybe older and younger women are equally likely to be manipulative. But without a doubt, older women (who do happen to be manipulative) are better at it. It's a skill that can only be refined and improved over time. Not lost or diminished.
instead of jaded I would say not willing to put up with bullshit
As for this, it's a matter of perspective. No one thinks of themselves as jaded. But again, my experience is that older women are simply more "world weary." Yes, I'm sure this feels like a reasonable defense mechanism from the perspective of the person who behaves like this. And in some ways, it is reasonable.
But that doesn't mean it's necessarily desirable or easy to deal with from the perspective of the other party (i.e. the guy). I understand and sympathize with older women who don't want to "put up with bullshit." And I don't personally want to deliver "bullshit" when dating.
But what's going to be better from my perspective? Someone who is cautious, analytical, suspicious, and critical? Or someone trusting, guileless, open, and non-judgmental?
Clearly the latter is more desirable to me.
That's not a knock against the former person. It's only natural that people (women and men) gradually develop those traits over time. But they're not appealing traits. At least to me. Or to most men. And I think the men who fail to detect those patterns in older vs. younger women are probably setting themselves up for failure.
[–][deleted] 0 points1 point2 points 4 years ago (1 child) | Copy Link
Actually the other way around. Started feeling entitled after buying me things to the point where I broke it off
Interesting. I guess there is also the phenomenon of older women becoming desperate because they know their time is running out.
Still, I would say that buying a potential partner gifts with the assumption that it entitles the giver to something is manipulative, so I don't think my above analysis was completely off base.
[–]FishyBricky 0 points1 point2 points 4 years ago (0 children) | Copy Link
How terrible 😂🤣
[–]Usual_Assistance8667 8 points9 points10 points 4 years ago (2 children) | Copy Link
Where did you meet her?
[–][deleted] 15 points16 points17 points 4 years ago (1 child) | Copy Link
Concert
Happy to hear this isn’t some OLD crap! You got this!
[–][deleted] 15 points16 points17 points 4 years ago (0 children) | Copy Link
Have fun- age difference can be exciting. A learning experience for both. Older woman are wiser and like clarity. Clear is kind always. Be yourself. Let us know how it went!
[–]immn00b 21 points22 points23 points 4 years ago (2 children) | Copy Link
What are you? 15?
[–]throwaway2492872 7 points8 points9 points 4 years ago (1 child) | Copy Link
40
[–]Bkri84 3 points4 points5 points 4 years ago (0 children) | Copy Link
Closer parking
[–]Kindly-Article7336 14 points15 points16 points 4 years ago (1 child) | Copy Link
This is the deal. I am an older woman and I like younger men. This is what I don’t like: Trying to come off as someone you are not. Saying things that a 20 year old girls might find cool. Like what’s up. It sounds stupid to us. Ask her lots of questions about herself. Be a gentleman. Come on too strong at the beginning she may not like it. Bring her flowers. Doesn’t have to be expensive. It’s the thought that counts. Keeping it casual means being yourself. Good luck with your date.
[–]HelpIntrovert 7 points8 points9 points 4 years ago (0 children) | Copy Link
Ive recently realized I like older women, I’m 22 and I appreciate the tips!
[–]Fluffy_Risk9955 8 points9 points10 points 4 years ago (4 children) | Copy Link
If the woman is much older she will play you like a violin and you won’t even notice it. This is not a psychologically healthy environment for you as a man. If you do it (yes it’s still loads of fun, trust me) time frame to max 3 to 6 months before ending it, because it’s playing with fire you don’t see the consequences for yet.
[–][deleted] 4 years ago (2 children) | Copy Link
[–]Fluffy_Risk9955 0 points1 point2 points 4 years ago (1 child) | Copy Link
Women are masters in human interaction and getting what they want. If she’s that much older, she’ll play him like violin and he won’t even notice.
[–]boxmail2800 6 points7 points8 points 4 years ago (0 children) | Copy Link
Ok… so what happened last time?
[–]BlacBlood 5 points6 points7 points 4 years ago (1 child) | Copy Link
Don’t speak too much. If you’re like 18 and she’s 40, don’t speak that much and just keep asking her mature realistic questions. Make her the center of attention. Rub her back and shit if you guys are in private while you ask her about her life and previous relationships lmao. If she’s more open minded and shit be playful and show her the youthful energy.
[–]jgesch -1 points0 points1 point 4 years ago (0 children) | Copy Link
I think he’s 42 and she’s 85 :)
[–]c2kink 2 points3 points4 points 4 years ago (0 children) | Copy Link
“Don’t talk” if really the advice… do talk, be yourself, ask questions and share. Nothing sexy about a man that doesn’t engage with me mentally.
[–]SupremeBBC 4 points5 points6 points 4 years ago (0 children) | Copy Link
Just remember that she's just another woman and you'll be ok
[–][deleted] 3 points4 points5 points 4 years ago (0 children) | Copy Link
Just be yourself & be cool .. if she’s attracted to you and interested then you won’t have to do or say much because she’ll take the lead in the situation ..
[–]Distinct_Face_5796 1 point2 points3 points 4 years ago (0 children) | Copy Link
Why? I am 39 and I would much have a hot 21 year old. Lol. They are hard to pull though, unless I am outside of the US.
[–]funkduder 2 points3 points4 points 4 years ago (2 children) | Copy Link
Be straight forward and earnest. If they're over 30 they've played the game and know what they want
[–]BJJ-Newbie 10 points11 points12 points 4 years ago (1 child) | Copy Link
If they’re over 30
OP would have to be 14 for her to be under 30 🙈
[–]funkduder -2 points-1 points0 points 4 years ago (0 children) | Copy Link
Thanks Capt. Obvious :D
[–][deleted] 2 points3 points4 points 4 years ago (0 children) | Copy Link
i actually think this requires less skill than someone younger, older women flirt the fuck right out of me and leave me baffled
[–]bradinthecreek 4 points5 points6 points 4 years ago (3 children) | Copy Link
Don’t talk. At all. Everything you say is going to sound dumb and immature to her. Be direct. Ask her if she’d like to come back to your place to watch a movie or something within the first 30 minutes
[–]ilhahq 26 points27 points28 points 4 years ago (2 children) | Copy Link
LOL. Cant you hold a conversation with an older person?
[–]Sylvariel 3 points4 points5 points 4 years ago (0 children) | Copy Link
Good point! Many people from age of somewhere around there mid twenties should probably be ably to have a reflected and proper conversation, even with people up in their fifties. At some point it is not necessarily more maturity, but only more experience in life, and sometimes even not that. Add on top a reflective mindset about the age gap and that's really all there is about it.
[–]bradinthecreek 1 point2 points3 points 4 years ago (0 children) | Copy Link
You are no doubt a master conversationalist
[–]SuggarTitsJones 0 points1 point2 points 4 years ago (0 children) | Copy Link
Older chicks are awesome for a bunch of reasons
[–]shusain2991 -3 points-2 points-1 points 4 years ago (1 child) | Copy Link
Ask for sex
[–]Electric_kundalini 10 points11 points12 points 4 years ago (0 children) | Copy Link
That's not how it works, Son
[–][deleted] -1 points0 points1 point 4 years ago (0 children) | Copy Link
Enjoy the mentorship
[+]ftdrain -6 points-5 points-4 points 4 years ago (1 child) | Copy Link
In my experience older ladies are desperate AF and have low standards
[–]inawlaah 2 points3 points4 points 4 years ago (0 children) | Copy Link
How did you gain experience?
Most of the older ladies I approach have a husband/bf. Maybe coz I try to pick them up from streets. Is there a place where I can find single ladies?
[+]cronasminate -13 points-12 points-11 points 4 years ago (0 children) | Copy Link
I honestly keep trying to hit up some milfs with some nice apartments so I can just visit different states and chill while being spoiled but I just keep getting young broke (but really hot) college girls who want to fuck in a car or by some river bank.
[–]Lotus_82 0 points1 point2 points 4 years ago (0 children) | Copy Link
She’s over 36, right?
[–]CaptnGoose 0 points1 point2 points 4 years ago (0 children) | Copy Link
Don't check his profile
[–]anicknameyo 0 points1 point2 points 4 years ago (0 children) | Copy Link
Be polite, respectful, communicative. When in doubt, just ask and don't assume things.
[–]Pedadinga 0 points1 point2 points 4 years ago (0 children) | Copy Link
Be upfront about wanting casual. If she’s more than twice your age, I can’t imagine she wants anything more than “casual” with you.
[–]inline6throwaway 0 points1 point2 points 4 years ago (0 children) | Copy Link
Older women dating younger men, that's a bit of an easier dating dynamic for the guy. Someone mentioned elsewhere that she's probably dtf. I would not disagree with that. It should be pretty easy going out with her and stuff. So something fun, have some drinks, make out, touch her as long as she's OK with it. Good luck! If you think she's beautiful, of she turns you on, let her know. Not just through words.
[–][deleted] 0 points1 point2 points 4 years ago (0 children) | Copy Link
I recall being seduced by an older woman some years ago. She was a good lover. Good luck my friend.
[–]Comfortable-Unit-897 0 points1 point2 points 4 years ago (0 children) | Copy Link
Get ready for one hell of a ride! Best six months of my life, and I learned a lot.
[–]flowr12 0 points1 point2 points 4 years ago (0 children) | Copy Link
I am turning 25 next month, my boyfriend is 39. I never liked him because of his age. I liked him for who he is, his age was just a characteristic of the person I really liked. So be yourself and don’t focus on the gap.
[–]KyleGuap 0 points1 point2 points 4 years ago (0 children) | Copy Link
Lol
[–]GalaxyBrainU 0 points1 point2 points 4 years ago (0 children) | Copy Link
Very important question that hasn't been asked/answered yet: how old are each of you??
[–]Cantsleepperson 0 points1 point2 points 4 years ago (0 children) | Copy Link
That sounds so hot. Congratz!
[–]OutsideFew2192 0 points1 point2 points 4 years ago (0 children) | Copy Link
My girlfriend is currently 42 and im only 24 and its the best relationship ive been in but at the same time the worst because when we have arguments it gets heated but we also work thru all of our shit. The only thing i can say as advice is stand your ground when she is argueing even if she is wrong she is right dont try to explain yourself because itll just look like your trying to have an excuse. Make her feel wanted but dont blow up her phone 24/7 trying to show you are super interested. Older women have lives aside from you so you have to show you have a life away fron her also. If you hit it off then it will flow naturally. All good things dont come easy and the moment she is sick of arguing if it gets to that really means she no longer cares. If this ends up being a thing shes not going to want to have to tell you what you need to do to please her. If money is a reason then it won't work although it does take money to maintain her your not obligated off the rip for any of her financial responsibilitys. All in all have fun take note of what she likes treat her with respect dint talk about your ex but if she does dont get jealous shes with you and your lucky to have this opportunity because man a lot of younger girls got life twisted so really treat her like a diamond but dont let her be the only thing in your life you care about. State your worth you have about yourself if she ever makes you feel worthless because obviously your not if she is interested in you come on my man you obviously do or did something to spark her interest and as long as it wasnt fake then be yourself and the rest will follow. If not at least you got the opportunity to be different from everyone else i believe with the right mindset and maturity that a situation like this is age is only a number can apply but don't bring up how much older she is and dont ever be ungrateful for her time spent with you
[–]ModeratorElbynerual 0 points1 point2 points 4 years ago (1 child) | Copy Link
Happy for you buddy but this post is breaking rule #1, sorry
[–][deleted] 1 point2 points3 points 4 years ago (0 children) | Copy Link
Ahh okay thanks will post in line with the rules next time
© TheRedArchive 2026. All rights reserved.created by /u/dream-hunter
[–]vroomvroomski 98 points99 points100 points (3 children) | Copy Link
[–]sublimeonskunk 9 points10 points11 points (0 children) | Copy Link
[–]HootingMandrill 3 points4 points5 points (0 children) | Copy Link
[–]what_it_do_bby 2 points3 points4 points (0 children) | Copy Link
[–]focus_flow69 133 points134 points135 points (8 children) | Copy Link
[–]LolaBijou 19 points20 points21 points (0 children) | Copy Link
[–]punittt 61 points62 points63 points (3 children) | Copy Link
[–]iiexistenzeii 18 points19 points20 points (1 child) | Copy Link
[–]punittt 6 points7 points8 points (0 children) | Copy Link
[–]VivaIlSesso 3 points4 points5 points (0 children) | Copy Link
[–]crackers-do-matter 1 point2 points3 points (1 child) | Copy Link
[–]focus_flow69 2 points3 points4 points (0 children) | Copy Link
[–]4goodluck -1 points0 points1 point (0 children) | Copy Link
[–]Segundaleydenewtonnn 25 points26 points27 points (0 children) | Copy Link
[–]grindforthegold 57 points58 points59 points (1 child) | Copy Link
[–]sublimeonskunk 7 points8 points9 points (0 children) | Copy Link
[–]ikeepon 59 points60 points61 points (3 children) | Copy Link
[–]Dakessian 3 points4 points5 points (0 children) | Copy Link
[–]getmeb 0 points1 point2 points (1 child) | Copy Link
[–][deleted] (6 children) | Copy Link
[–]kellykebab 4 points5 points6 points (5 children) | Copy Link
[–]Pedadinga 11 points12 points13 points (1 child) | Copy Link
[–]kellykebab 0 points1 point2 points (0 children) | Copy Link
[–][deleted] 0 points1 point2 points (1 child) | Copy Link
[–]kellykebab 0 points1 point2 points (0 children) | Copy Link
[–]FishyBricky 0 points1 point2 points (0 children) | Copy Link
[–]Usual_Assistance8667 8 points9 points10 points (2 children) | Copy Link
[–][deleted] 15 points16 points17 points (1 child) | Copy Link
[–]VivaIlSesso 3 points4 points5 points (0 children) | Copy Link
[–][deleted] 15 points16 points17 points (0 children) | Copy Link
[–]immn00b 21 points22 points23 points (2 children) | Copy Link
[–]throwaway2492872 7 points8 points9 points (1 child) | Copy Link
[–]Bkri84 3 points4 points5 points (0 children) | Copy Link
[–]Kindly-Article7336 14 points15 points16 points (1 child) | Copy Link
[–]HelpIntrovert 7 points8 points9 points (0 children) | Copy Link
[–]Fluffy_Risk9955 8 points9 points10 points (4 children) | Copy Link
[–][deleted] (2 children) | Copy Link
[–]Fluffy_Risk9955 0 points1 point2 points (1 child) | Copy Link
[–]boxmail2800 6 points7 points8 points (0 children) | Copy Link
[–]BlacBlood 5 points6 points7 points (1 child) | Copy Link
[–]jgesch -1 points0 points1 point (0 children) | Copy Link
[–]c2kink 2 points3 points4 points (0 children) | Copy Link
[–]SupremeBBC 4 points5 points6 points (0 children) | Copy Link
[–][deleted] 3 points4 points5 points (0 children) | Copy Link
[–]Distinct_Face_5796 1 point2 points3 points (0 children) | Copy Link
[–]funkduder 2 points3 points4 points (2 children) | Copy Link
[–]BJJ-Newbie 10 points11 points12 points (1 child) | Copy Link
[–]funkduder -2 points-1 points0 points (0 children) | Copy Link
[–][deleted] 2 points3 points4 points (0 children) | Copy Link
[–]bradinthecreek 4 points5 points6 points (3 children) | Copy Link
[–]ilhahq 26 points27 points28 points (2 children) | Copy Link
[–]Sylvariel 3 points4 points5 points (0 children) | Copy Link
[–]bradinthecreek 1 point2 points3 points (0 children) | Copy Link
[–]SuggarTitsJones 0 points1 point2 points (0 children) | Copy Link
[–]shusain2991 -3 points-2 points-1 points (1 child) | Copy Link
[–]Electric_kundalini 10 points11 points12 points (0 children) | Copy Link
[–][deleted] -1 points0 points1 point (0 children) | Copy Link
[+]ftdrain -6 points-5 points-4 points (1 child) | Copy Link
[–]inawlaah 2 points3 points4 points (0 children) | Copy Link
[+]cronasminate -13 points-12 points-11 points (0 children) | Copy Link
[–]Lotus_82 0 points1 point2 points (0 children) | Copy Link
[–]CaptnGoose 0 points1 point2 points (0 children) | Copy Link
[–]anicknameyo 0 points1 point2 points (0 children) | Copy Link
[–]Pedadinga 0 points1 point2 points (0 children) | Copy Link
[–]inline6throwaway 0 points1 point2 points (0 children) | Copy Link
[–][deleted] 0 points1 point2 points (0 children) | Copy Link
[–]Comfortable-Unit-897 0 points1 point2 points (0 children) | Copy Link
[–]flowr12 0 points1 point2 points (0 children) | Copy Link
[–]KyleGuap 0 points1 point2 points (0 children) | Copy Link
[–]GalaxyBrainU 0 points1 point2 points (0 children) | Copy Link
[–]Cantsleepperson 0 points1 point2 points (0 children) | Copy Link
[–]OutsideFew2192 0 points1 point2 points (0 children) | Copy Link
[–]ModeratorElbynerual 0 points1 point2 points (1 child) | Copy Link
[–][deleted] 1 point2 points3 points (0 children) | Copy Link