Dating an older women when younger then 38.

So matched with this pretty milf on tinder and want to date her. But I'm 19 and she's 38, you think it's okay for me to do it. She's super cute and doesn't look a day over 25. We'll look really good together, like a mid-20's couple. Anyway, not looking to get judged for this but am posting this publicly to get dating ideas.

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Comments (62)

  • Intern in RE - Comm
Apr 7, 2021 - 9:39pm

I love Isaiah, this isn't me bashing him. But I think she's super cute and ever since her man walked out, she could use a boy like me. Plus her daughter, Stacy, is super cute as well. She's my hedge if this goes south. I'd love to start a family with her.

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  • Associate 2 in PE - Other
Apr 7, 2021 - 9:47pm

Go for it bro. Matter of fact, anytime someone questions you on it, give real vague, almost incoherent replies and semi freak out when you get MS. 

Oh yeah, don't forget to sprinkle granola bible quotes and verses to make the haters reconsider your POV.

  • Intern in RE - Comm
Apr 7, 2021 - 9:52pm

"Love thy neighbor motherfucker" - the Bible.

  • Intern in RE - Comm
Apr 7, 2021 - 10:11pm

I do live with my parents, they are super religious Catholics. I'm kinda worried about it. Bringing home a 38 year old woman when 19 is... not common. But I made this thread for dating ideas, please stop talking about Isaiah (this is not related to that) and give me some dating ideas. 
 

Apr 7, 2021 - 10:15pm

Are you able to stay out all night otherwise she will not stand for it. Beyond that I dated some older ladies but I was 22-25 at time. Truly no joke you can watch "sex in the city" re-runs and vast majority of that shit is real. Women that age just want small details taken care of and to relax and have fun. She will do all the planning/big things/night outs/trips. You just there to entertain and be 100% supportive basically. Making a simple home cooked meal, taking time to listen to her beefs of the week and so on. It's the opposite of the 19 year old girl that wants everything to be done for her.

Apr 8, 2021 - 7:56am

I do live with my parents, they are super religious Catholics. I'm kinda worried about it. Bringing home a 38 year old woman when 19 is... not common. But I made this thread for dating ideas, please stop talking about Isaiah (this is not related to that) and give me some dating ideas. 

Dad is going to give you a wink of approval and your mom will think that she failed as a parent.

http://www.series65examtutor.com
  • 2
  • Intern in HF - Other
Apr 7, 2021 - 10:26pm

Send it! When I was 19 I studied abroad in Australia and ended up blowing my shot with one of the top 5 most beautiful women I've ever seen. In a drunken stupor I ended up going home that night with a 43-year-old Irish woman named Lou. She wasn't particularly good looking and the experience wasn't particularly enjoyable but I'll never forget it or the **** my roommates gave me after I rolled up to class in an uber she ordered me the next morning in last nights clothes smelling like a concoction of scotch, cigarettes, and sloppy drunken sex. 

Apr 7, 2021 - 10:49pm

This is tough, as I'm used to seeing a shirtless picture of yourself and a picture of the woman in question when asked to evaluate relationships. I do not think I will be able to provide a concrete answer due to the lack of information, but I would say you're in the clear. 38 and 17, a la Matt Gaetz, is downright terrible, but 38 and 19 is a world of difference. We are talking 2 whole years, and 2 was my number on the Spurs, Raptors, and now the Clippers, so I think that's as good a sign as any. Good luck!

I’m a fun guy. Obviously I love the game of basketball. I mean there’s more questions you have to ask me in order for me to tell you about myself. I'm not just gonna give you a whole spill... I mean, I don't even know where you're sitting at
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  • Intern in RE - Comm
Apr 7, 2021 - 10:58pm


I won't a post a picture of her. But this is me. Not bad eh.

Apr 8, 2021 - 12:41am

I'm jealous

I’m a fun guy. Obviously I love the game of basketball. I mean there’s more questions you have to ask me in order for me to tell you about myself. I'm not just gonna give you a whole spill... I mean, I don't even know where you're sitting at
Apr 8, 2021 - 4:47am

Lmao. Based

Never discuss with idiots, first they drag you at their level, then they beat you with experience.

  • Intern in AM - Equities
Apr 7, 2021 - 11:32pm

I mean go for it, if you're this excited over a tinder match to where you needed to talk about it with your online buddies then you probably should stick it in.

That goes for you too isaiah. 

  • Intern in RE - Comm
Apr 8, 2021 - 10:25am

Well we already slept together once (didn't do the sex thing though because I'm catholic), matched over the weekend and she already introduced me to her daughter, we're thinking about moving in together. Thoughts?

  • Intern in RE - Comm
Apr 8, 2021 - 10:26am

Yeah I remember last year when I graduated my English teacher and I hooked up over the summer a few times, she was 43, god she's so hot.

  • Intern in RE - Comm
Apr 8, 2021 - 10:29am

 Nah this ain't the move. See when you're young you want to go for older women but when you get older you got to start going younger. 

  • Intern in RE - Comm
Apr 8, 2021 - 10:31am

See my pic above, don't want to post a picture of Maria for privacy reasons. Just know she's hot, like a lot hotter than your mom.

Apr 8, 2021 - 11:04am

Don't let anyone stop you from what you want to do, just think about the long term viability, i.e. kids are a no go unless you get goin like right now, everyone has an expiration date when it comes to looks, and most of all, she's a person too with feeling and emotions.

On the flip side, can confirm women in their 30's are a solid smash, not sure what it is, but the combination of experience, focus on physical fitness, and a bit of life maturity makes for a good night, and remember, don't be silly, wrap your willy.

  • Intern in RE - Comm
Apr 8, 2021 - 11:27am

Thank you all for the reply's, was hoping for some more dating ideas and things we can do together but this is still good so far. Man, I feel so much better about everything, my boss still farts on me but at least with Maria, I have some semblance of peace.

Apr 8, 2021 - 1:00pm

Bro your map is totally perfect. Is she well regarded in her catholic community? I hear this negates any pedo vibes.

I also love that you're sourcing dating ideas on a finance forum - brilliant - but it would be really helpful if you could post her pic.

Just had my trade dispute rejected by Schwab for a loss of 35k. This single issue alone should be a gigantic red flag to anyone who trades on their platform.

If they have a system error, and you do not video record your trading (they actually said this), they will not honour their fuck up. Switching everything away from them. Fuck this company.

  • 1
  • Intern in RE - Comm
Apr 8, 2021 - 1:11pm

She's not catholic, she's a Mormon, non practicing though. My only concern is our children, which we are planning to have in the next year or so. I want them to go to a catholic school but she's not having it. It's got me really concerned because we got off to such a great start a week ago, but this is just god testing our love for each other. 
 

I have no map, I just let life take me wherever it wants to take to me. That is the only way to live, in service of god and to be his slave.

Apr 9, 2021 - 5:48am

Not sure if trolling, but whatever... It reminded me of a story of mine. Also 19, she was 32. I was interning at this 40 people F&B operator, building some pricing database. Indirectly had some exposure to her (COO), but always in meetings. On the last day, I made my move, obviously thinking I had no chance. We agreed on a casual dinner as a "End of internship" thing. Very flirty thing, so I saw only green lights and kept on playfully advancing... All until she said: "seems you are not afraid of taking it to the next level, neither I am". Jeezz, I love this no nonsense of women who know what they want and aren't playing games! 

In terms of dating suggestions, when out, mostly movies, restaurants, bars, walks. Did lots of cooking at her place, movies on the couch, she also had a house outside town in the mountains, so went there. Not a lot of interactions with friends (hers, as I was enjoying every minute alone with her), but a few times went and met some at their places and hosted them at hers. 

Pro tip: my parents didn't know and only a few friends knew about it. I had a good friend w was in the know, so for weekends out with her, I told everyone (my parents included), I was staying at this friend's house for the weekend... Best weekends ever. I miss this feeling of adventure of doing something unconventional and winning the attention of someone so "adult" when still being on my teens. She was lovely and also cute, not necessarily smoking hot though.

In terms of having a family with her, I would advise you against it. Live your life a bit, grow up, and then you can better decide on parenting.

Good luck, enjoy it, an experience for life.

Apr 10, 2021 - 2:02am

Ha ha... At least, -if done so- you will have nice recollections of that relationship and avoid having kids with 20 or 21.

Btw. The happy Volvo owner is the missus (all about safety for our biggest investment, our kids)... So yes, it makes me a happy Volvo driver, when I get to drive it (mostly for long trips, evenings, when a glass of wine was involved over dinner -aka the designated driver)... A glorified Uber gig ha ha!

  • Associate 2 in IB - Ind
Apr 10, 2021 - 10:41am

I've had my flings with women 10 years + older than me. I've quickly learned age is just a number, what matters is a person's mindset. I've hooked up with a high school teacher 10+ older than me that acted like a princess and was extremely immature. I've also met another older woman who was really smart, mature, and fucked my brains out. 

Have fun, use condoms, let them mentor you ;)

Apr 11, 2021 - 3:58pm

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

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