- This topic has 1 reply, 2 voices, and was last updated 11 years, 8 months ago by
April Masini.
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December 21, 2013 at 10:01 pm #6391
ManUp2012
ParticipantHi April, I need some advice on my situation with an older woman. I am currently 23 and she is 39. For the purposes of making this talk easier – her name is Amy
How We Met:
We met at a hackathon (a competition where you have to create an idea and develop it into a business model and present it to investors in 48 hours). She was beautiful and had a great idea. I joined her and, together, worked (and flirted) and won 3rd place.
She showed a lot of attraction towards the end – (when i whispered in her ear about soemthing, i could feel her putting her head on my head, gently careening my shoulder when we talked, etc.Aftewards, I walked her to her car, she hugged me and gave me her number. Promptly later, I texted, i told her I told her to keep in touch and let me know if she wanted to do stuff more about the business or just to hang out. She responded with “I’d love to hang out
🙂 ”Friday Night Out 2 Weeks Later:
We chatted a fair amount through text about a a lot of things and and learned more about each other. Finally, she asked me around thanksgiving if I want to go see a movie with her after she couldn’t come out with me to go salsa-ing.
We went, and afterwards she asked me if I wanted to grab a drink. One drink become a few drinks, and we talked and chatted and flirted from 11pm to 5am. We talked about everything – her life, her interests, everything. At one point, we talked about our sex lives, how she hasn’t had sex in a few months due to a bad breakup, hasn’t dated anyone, etc. She also told me how attractive and gorgeous she thought I was, how confused she was that I was single, and (after asking about my type of penis – whether it was circumsized or not) – she told me how women of her age would love to have a lover of that sort. She also said “I don’t know what type of connection we have, but I love the energy” or something like that. She even brought up the fact that she believes age doesn’t matter for dating, etc. I paid for the drinks.
At the end of the night, i walked her to her car..didn’t make a move but we definitely just sort of hung out and she said how much of an amazing time she had. We were both way too far from our houses so it wouldve been a bit awkward to come back to my place. Afterwards, I got a text from her
“Just pulled into home. Thank you for an amazing evening! Can’t wait to hang out again!!! I had an incredible time!” xoAnyway, afterwards, we constantly text each other about everything…Making her laugh, etc. She sent me a christmas letter with “You’ve been an unexpected and delightful addition to my life! Love our friendship and our energy.” I wasn’t sure how to respond but essentially sent her a small gift with a card with the face of her favorite actor (mario lopez) and some inside joke.
She texted me when she received it with a “OMG!!! Just came home to the most thoughtful / funny from you!!! Huge Hug!!! Thank you! Muah!!!!” – and she asked me to get a drink with her the next day.
Again, we hung out, it was a little less flirty but we talked and chatted and laughed for another 4 hours. I paid for the drinks. I sort of pussied out and didn’t ask her out on a proper date walking her to her car. But, finally growing a pair, I called her as she was driving back and called and asked her “Hey quick question – once you’re back from NY, would you like to go out for dinner?” She responded with “Yes! Of course!”
I’m sort of happy but not sure if she gets that it’s essentially a date or if she sees me a just a friend, or maybe even a fuck buddy. She has talked about going out and dancing Salsa with her and maybe going to concerts together. She’s told me how she thinks i’m way cuter than Ryan Gosling, after me sending her one of those “Hey Girl” memes, etc.
Earlier today, she told me she was giong to a cocktail party and was excited to see some of her girlfriends and was getting ready “a bit excessively”. I responded with “Trust me Amy you don’t need to excessively prep to look stunning at a cocktail party.” she sent a Blushing smiley emoticon.
It’ hard to know what she’s thinking. A lot of the time she initiates texting, but sporadically she says “my friend.” she did say friendship” in the card – but i find it unusual for a remarkably successful and beautiful lady of her age even wasting time talking to a 23 year old like me.
We will be seeing each other again, probably for that dinner. I’d like to think I still have a chance with her…but another part of me thinks this is a fools errand and she’s just gonna say she enjoyed my company as a friend.
December 22, 2013 at 2:43 pm #29062April Masini
KeymasterDo you have a question for me? 🙂 -
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