Interesting thing happened to me...What should I do now? (confused)

CH812

Active member
May 15, 2004
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Ok had an interesting story happened to me over the weekend and now I am a little twisted inside and dont know what to do next...

Since I had alot of work to do I decided this weekend I was going to dedicate to getting some deep work done, my plan was to start on Saturday afternoon after I had lunch. For lunch, I decided to get some takeout at one of my favourite food spots in the outer boroughs of the city. I got in my car and headed there to pick up my takeout order. After arriving at the restaurant , which is located in a strip mall, I picked up my food and was walking back to my car when I saw a woman who looked familiar. We made eye contact so I figured she recognized me as well. As I walked by her I said "Hey I know you" .

She is a girl who used to work at strip club about 10 years ago and who I hooked up with p4p on a couple occasions. She was always exactly my type, she has dark curly and very curvy (especially the lower half of her body) anyways shes older now and a little heavier but still very attractive in my eyes. I also kind of fell for her in the past, we shared some good times and did have some great sex so I did kind of get a little bit heartbroken when I tried to pursue a relationship with her but she basically explained to me that since we met inside the club and I knew her from the club it could only be about business between us so I respected that and afterwards distanced myself from her.

But when we saw eachother we chatted I told her it was nice to see her after so long and that I recently just moved back into the city after being gone for some years. She said she was waiting for her Uber to arrive so I told her to cancel the Uber and I will give her a ride. We then got into my car which I have to admit is an impressive car for women who are into what kind of car a man drives. While driving in my car I asked her where I should drop her off and she responded "I dont even know" and then asked me what my plans were. I told her I had plans to work and just was here to pick up my lunch. She then asked if she could hang out with me and I said sure if she doesn't mind going back to my place where I needed to work. She said sure, so we drove back to my place.

After arriving at my place I offered her part of my lunch but she declined and instead asked for something to drink. I had some Crown Royale so I poured her a glass with some ice and she drank while I finished my food. I then I showed her around my apartment and told her I needed to work in my office but I have a loveseat sofa in there so I told her she could sit with me there and listen to music/watch TV while I worked. After about another hour or so of me working and having some small talk with her she asks me "Do you mind if I take a shower?" I replied no and got her a fresh towel. After her shower she asked if I had something comfortable she could wear inside my place so I gave her an oversize sweatshirt I had and after that whe was just hanging around with me in my office wearing my sweatshirt and her thong underwear. At this point I really couldn't concentrate on my work anymore so I had a drink with her and sat with her on the couch. We chatted more until our lips finally met... We started making out which was crazy to me because when we hooked up before p4p she would never kiss me we just did the deed. but now here we are making out and touching eachother. Eventually we headed to my bedroom and the rest goes without saying.... After that we watched some movies, had a few more drinks and ordered food later in the night. She ended up staying over for more passionate sex that night and same thing on Sunday.... She ended up staying with me until Monday morning when I dropped her home.

She said she lives with her mom and takes care of her because she currently has some health issues, where she lives is a modest rental apartment building and job wise she said when not taking care of her mom she has a dog walking business and also is a waitress in a restaurant.

Since she left I haven't been able to stop thinking about her and the couple nights of passion we had, we have texted back and fourth since that night and she wants to see me again over this weekend coming up (so far has also not asked me for any $$$ nor has she implied shes looking for that) but I still know what kind of past she comes from and don't know if I want that especially since where I am in my life and career right now. And she did reject me before and my rule has always been if a girl rejects me I just consider her dead (Mr. Wonderful style) and move on.

But this time with her feels a little different especially considering the chemistry we have, so any advice on what I should do next? Should I risk my feelings with this girl or just have fun? Or maybe just enjoy the memory of the couple nights we have but cut her off? I am especially interested in what some of the ladies think I should do... Anyways if anyone has any thoughts or any advice to share I would love to hear it. Thanks in advance.
 
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newguy2201

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Nov 29, 2025
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Why not stay open to whatever possibilities are there? A lot can change in 10 years. She's not the person she was and neither are you.

It sounds like you guys have the makings of a good thing. Date her for a bit and keep an open mind

Life's too short for "Mr Wonderful" (who??) games and hard rules. Life's hard enough without making it harder with black and white thinking

What's the harm in seeing where it goes?
 

xix

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"Psychology Today".. is next door over.


 

greensquare

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Aug 23, 2026
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Cut her off and move on. She's not doing well financially or so compared to you it seems. You should know why she did all this. In time she'll most likely ask for funds or vent to you about her financial situation hinting stuff.

I'd personally move on...especially years ago she said she keeps things business.

Doesn't matter if she thinks diff now.

Maybe I'm cold like that. But do what makes you happy. If it turns bad then live and learn.
 

CH812

Active member
May 15, 2004
229
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Downtown Toronto
Cut her off and move on. She's not doing well financially or so compared to you it seems. You should know why she did all this. In time she'll most likely ask for funds or vent to you about her financial situation hinting stuff.

I'd personally move on...especially years ago she said she keeps things business.

Doesn't matter if she thinks diff now.

Maybe I'm cold like that. But do what makes you happy. If it turns bad then live and learn.

Yea that is kind of what I am thinking as well, she might be setting me up for the long game where she gets me to fall for her again and then asks for money down the road.
 

greensquare

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I have 0 trust for that. But that's me.

If she wants to do p4p and you're down for it then do that.

I wouldn't waste time and energy starting something with her.

See seen your vehicle and place. If you weren't doing well she might have told you in the vehicle where to drop her off.

Who in their right mind would be like IDK?
 

CH812

Active member
May 15, 2004
229
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Downtown Toronto
I have 0 trust for that. But that's me.

If she wants to do p4p and you're down for it then do that.

I wouldn't waste time and energy starting something with her.

See seen your vehicle and place. If you weren't doing well she might have told you in the vehicle where to drop her off.

Who in their right mind would be like IDK?
Lol you got a point she still has that kind of stripper flighty mentality

and I am a responsible disciplined type of man.
 

greensquare

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Aug 23, 2026
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When she got in your vehicle and said IDK then said if she can come back to your place that already tells me what most likely would happen and did. Sex.

Your ride was enough to make her wanna spend time with you.

Pick her up in a used 2001 vehicle next time and rent a small average BnB and tell her you downsized and surely enough she'll say she wants to go back home. Probably would say she has a headache or tummy issue.
 
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xix

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CH812

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May 15, 2004
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Downtown Toronto
Kind of hard to put the toothpaste back in the tube now she has already seen my car and where I live and knows what kind of lifestyle I live.

But I definitley should run some kind of test just to see what her intentions are and if she fails just cut her off right away
 

greensquare

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Do what xix said. Over text act weird. Tell her you're feeling down. Slide in financially things have turned. Then ask her if she still wants to hangout. Be like I can take the public bus and pick you up. Then we can grab something to eat by taking the bus.

If she says yes...then see how things play out. Tell her the dealership took the vehicle back.
 

xix

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Ok had an interesting story happened to me over the weekend and now I am a little twisted inside and dont know what to do next...

She said she lives with her mom and takes care of her because she currently has some health issues, where she lives is a modest rental apartment building and job wise she said when not taking care of her mom she has a dog walking business and also is a waitress in a restaurant.
The bold says it all.
What would anyone here say if they heard the famous football player from your own high school is living at home after coming back from a weird 20 year absences?

I run for the mountains.
 
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greensquare

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Back when you did p4p she had funds hence the no kissing and stuff.

Now look at the game she's playing. Kiss kiss. Touch touch. Ohhh I'm at your place...can I shower? Hehehe...gimme a break...I wasn't born yesterday.
 

LTO_3

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Aug 27, 2004
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Proceed very carefully and slowly & think with your big head and not your dick's head. Times have changed for both of you and if she's into you, you may end up paying for more than you expected or wanted. If it turns into a BF/GF situation is that something you want but still want to see SPs, then you may have a potential problem balancing both. If she eventually starts asking to borrow some money, get ready to run away...quickly.

LTO_3
 

CH812

Active member
May 15, 2004
229
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Downtown Toronto
Thanks for all the great feedback gents. I actually just thought of a test I can run on her when we meetup this weekend, I will report back and let you know how it goes......
 

greensquare

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I wouldnt even wait till the weekend. By tmrw afternoon over text I'd say the vehicle is gone and mention the public bus over text to pick her up. Why waste time for an in person meet if over text she backs out over a public bus?
 

SlitherBeth

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I might suggest just asking this woman where her head's at. Tell her you're not interested in resuming your p4p arrangement, but casual sex and low-stakes dating fun sound good to you (unless you're looking to date someone more seriously?) Hot passionate sex is worth having for its own sake, and there's nothing wrong with building a relationship just for that, but you two definitely have to be in the same page.

It seems to me that unless she gives you a reason to question her motives, like starting to lean on you for money or to pay for things, you can assume she's acting in good faith. As mentioned, ten years is a long time and people can certainly change quite a bit in that time. I tend to trust people unless they give me a reason not to, and you and she have history that probably already colours your opinion of each other. I might give her a chance, but remember that you are indeed taking a chance.
 
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CH812

Active member
May 15, 2004
229
40
28
Downtown Toronto
I might suggest just asking this woman where her head's at. Tell her you're not interested in resuming your p4p arrangement, but casual sex and low-stakes dating fun sound good to you (unless you're looking to date someone more seriously?) Hot passionate sex is worth having for its own sake, and there's nothing wrong with building a relationship just for that, but you two definitely have to be in the same page.

It seems to me that unless she gives you a reason to question her motives, like starting to lean on you for money or to pay for things, you can assume she's acting in good faith. As mentioned, ten years is a long time and people can certainly change quite a bit in that time. I tend to trust people unless they give me a reason not to, and you and she have history that probably already colours your opinion of each other. I might give her a chance, but remember that you are indeed taking a chance.
These days when it comes to my time and peace I am alot less risk adverse but you got a point about hot passionate sex! so keeping it casual sounds like a good idea and if she shows me any red flags Ill just immediately cut her off.
 
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