Help dating older woman

[manfromitaly]

OP: this should be a slam dunk.

Why don’t you invite her to your place make up some excuse about needing help with decorations or something.

Make dinner, make some drinks and escalate.

Also, can I ask what country are in?

Unfortunately I can't invite her to my house, I live with my grandfather and she knows it, and even though I think she would agree to having sex it would be too obvious, I think if it has to happen, it will happen at her house We live in Italy anyway

 

[Pierce Manhammer]

Fortune favors the bold.

Bust a move.

Ask her to go for the weekend to the beach out of town. Problem solved.

 

[BillyPilgrim]

Fortune favors the bold.

Bust a move.

Ask her to go for the weekend to the beach out of town. Problem solved.

In France if you can, OP. Not Italy.

 

[Passion69]

Op this is a rare gift from the heavens that almost landed in your lap, you need to get out of your head a little bit and just relax man, have fun and see where it goes. If nothing happens so be it, take it as a learning experience. But shoot your shot otherwise you will regret not taking a chance.

 

[ThisIsSparta]

Op this is a rare gift from the heavens that almost landed in your lap, you need to get out of your head a little bit and just relax man, have fun and see where it goes.

No, he really shouldnt.

A 50 y.o. woman is not a rare gift from the heavens.

If anything that women should see him as a rare gift from the heavens and treat him accordingly.

We tell guys here to walk away from young women that make them wait. Waiting for a 50 y.o. to make up her mind over weeks and months is just acting like a needy simp.

For all we know that woman could have no sexual interest at all and just enjoys the attention of a young man while she strings him along over some time while OP is wasting his time.

She is using her mother as cokkblock, if she had desire for him she should have been all over him as he made his interest more or less clear.

What OP should do is move on if nothing happens on her birthday.

 

[Scaramouche]

Hi Man from Italy,
The two best Days to plug a Woman are Christmas Eve and their Birthday the logistics make the latter seem very difficult if not impossible as Mum is still around....Pity that....Coincidentally I have always found a tastefully written Card for these two Days can work wonders! So note the date down.

 

[manfrombelow]

A healthy, normally-functioning male at the age of 32 should not be simping after a 50-year-old woman.

 

[ThisIsSparta]

the logistics make the latter seem very difficult if not impossible as Mum is still around....Pity that...

Women only make it difficult for men they have low interest in. Meanwhile they will swim across the amazon river to jump on Chads dyck.

There is no substitude for genuine desire.

The best fvcks i had were with women that wanted me from the start. The ones that needed to be convinced more often then not just sucked in bed and most of the time not even my dyck.

 

[MixedMutt00]

, I didn't have the opportunity to escalate, she invited me anyway to stay and we ate together, unfortunately I discovered that she is hosting her mother and that she would be home during the evening, so we sat on the terrace for a while, unfortunately she only has single chairs so it was more difficult to create physical contact, little some time later his mom came back so I left.

pull the chairs as close as possible when you both sit down, grab her legs and throw them across your lap. do it exaggeratedly and playfully, she'll laugh but she'll keep her legs on your lap.

No offense to her, but she probably doesn't have many other guys calling her pretty; she'd LOVE for you to compliment her, especially with all the time she enjoys with you clearly (You're goal is to build attraction, not be a simp so don't over-compliment) Remember, you're the Catch, the Great Guy. Wait any longer and she WILL look for someone else.

Then you get to here all about her new, young man and how he smashes her amazingly, you know since you guys talk about sex but you never made the move so she thought you guys were just friends.
People are reflexive; act like there's a problem and she will act like there's a problem. Show her YOU ARE cool and confident and she'll match your vibes homie

 

[MixedMutt00]

I was 21 and hooked up with a 50yo, and she was calling me every now and then, I'm sure she would've dated me. People like us, we're cool and have options man. She knows it, but she's got em' too.

Don't think negatively; worst case scenario: you're porking some other 21yo 16 months from now having amazing sex

 

[Learning Curve]

Guys, I need some advice, for a few years now I've been attracted to a woman much older than me who, among other things, is the aunt of a friend of mine, and this has always held me back, we talk on the phone sometimes, a a couple of times she also invited me to her house for a coffee, one of these times I let myself be overwhelmed by emotions and while I was hugging her I revealed that I felt attraction (very serious mistake).

She replied that she already knew, having said that I never had the courage to take any more risks.

Last week we went out to eat together but I didn't do anything apart from some hugs and physical contact.

Tonight she invited me for an aperitif and I gladly go there but I feel like I'm lying to myself. Because I really would like to have a more intimate relationship, I like it too much. I would like to take more risks at the cost of losing her and ending the relationship. What would you do?

Dude, she is older than you she knows what she wants.

She is not stup1d of inviting you out, go for the kill. Tell her to go to your place or her place and make the move.

What are you waiting for?

 

[Dr.Suave]

A healthy, normally-functioning male at the age of 32 should not be simping after a 50-year-old woman.

There, fixed it.

 

[Learning Curve]

There, fixed it.

Funny sh1t right here.

I don't get the 50 year old choice. is like we are out of women this days and guys go for what ever they find.

 

[BillyPilgrim]

Funny sh1t right here.

I don't get the 50 year old choice. is like we are out of women this days and guys go for what ever they find.

OP is in Italy

 

[Pierce Manhammer]

I understand that many here want to uplift the OP and feel that their own approach to life is better.

But he is ridiculously attracted to this MILF; he should just try to smash it.

I do not understand why so many men here are always so quick to judge what attracts other men and quick to put down a guy for what he wants.

The OP asked for help getting her to have sex with him, we should focus on helping him do so - not judge him for his choices, which after all are HIS choices.

 

[I_have_BDE]

A healthy, normally-functioning male at the age of 32 should not be simping after a 50-year-old woman.

Maybe if they looked like Melania Trump or something. Otherwise NO!

 

[manfromitaly]

Sorry I had a busy days, thanks again for the advice I will try to do my best in the next meeting, as for those who wrote negative comments, I don't understand what the problem is, she is a beautiful woman, very attractive for her age, why shouldn't I try to bed her? The women I've been most comfortable with in both reading and relationships were all older than me

 

[MatureDJ]

Use this line:

I think it's time to take a shower.

 

[itouchyou]

I sympathize with OP. Don't know how hot this 50 year old is, but the one I met was a straight up 9 that looked 10 years younger. Married unfortunately.

 

[BillyPilgrim]

I sympathize with OP. Don't know how hot this 50 year old is, but the one I met was a straight up 9 that looked 10 years younger. Married unfortunately.

OP's 50 y/o is Italian unfortunately, she may as well be married.