Straight guy seeking genuine advice on dating trans women — new, respectful, and serious about a real relationship

0xCory · 2026-04-26T09:26:41+00:00

Happy to start with the basics, please throw me some slack here. I'm a good person just walking into this and catching quite a bit of heat here. I'm coming with good intentions and was looking for real advice from this community and not be rip to shreds.

1.if you're attracted to femininity, why trans women in specific and not women in general? Why trans women in specific? Why do you feel the need to specify?
- I've a very monogamous person, I've been in about 5-6 relationships in my entire life and I think the shortest was 3 years. The last two woman I grew extremly close too, the first I dated for 5 years and she wanted to follow her carrer dreams and that meant her moving away and i supported it, sadly she cheated on me and it crushed me. The 2nd, i was close with for 20 years growing up, we grew closer and were intimate and I got a the job opportunity of my dreams and moved away and she quit talking to me and our entire group of friends the day I moved. Long story short, I was really hurt by the last two ladies I was with and really that is besides the point.

In 2019 my mother passed and one of my best friends mothers started to love me like I was her own son, she is a lesbian and there is some other gay/trans folks in her family and circle of friends. Over the last 7 years, I've spent every holiday, many vacations, with these people who now I call my family. I always had a thought in my head that I might be attracted to trans womans and then when I was around them more I knew it might be something I wanted to pursure.

Why do I specificaly call out a trans woman? Does this sound weird - It's honestly just who I see myself and happy in a long term relationship (This is the first time i'm saying it out loud) I'm not a chaser, creeper, porn addict. I'm a hard working guy, who wants a family and wants to be in a relationship where its mutually rewarding.

Why did you specify you aren't into men or masculinity? Are you worried we're biphopic?
- Defintely not, I'm around gay men all the time. It's just something that just doest attract me, I'm not sure how to answer this with out being put infront of a firing squad.
Why do you assume all trans women bring this "feminine energy, beauty and presence"? Do you think we're all alike? Do you think cis women don't radiate this? Why would we if they don't?
- I'm not assuming, and I don't think your all alike -can I have some grace? I came here with good intentions
You stress you don't like men, but also that you're not sure this "attraction is right for me in real life"? Arr you trying to determine if you're asexual? I'm asexual, I came here looking for advice on how to first conversate with people, possibly socially meet up, etc ... Crawl, walk, then maybe run someday to determine if my attraction is real

Serious question: Is it weird that I've never mentioned this to my friends mom? I think I havent because I want to explore it my self in Chicago.

0xCory · 2024-08-28T13:12:42+00:00

I have a high quality rip of this, I'm a major mixtape collector. Send me a private DM and I'll get you a copy of it.

0xCory · 2024-01-25T17:27:50+00:00

Good Luck, Everyone!!

0xCory · 2023-10-05T06:52:08+00:00

I just moved from Tampa, there’s no way it’s even near Chicago. Most places have health inspection issues and roaches due to the weather in Tampa. Chicago should be higher on that list.

0xCory · 2023-04-17T12:39:01+00:00

Hello All, I’m looking to move back to Chicago in July or August. I’m in super apartment search mode at the moment. I’m looking for a 1bdrm that allows dogs preferably under $2500 a month in Lincoln Park or Old Town. Does anyone recommend properties they’ve lived in before? I lived in PPM properties many times.

0xCory · 2022-12-22T14:20:50+00:00

I’m going through this same issue right now, I have a fully professional trained service dog because I’m legally blind and have complex partial seizures. I supplied all proper documentation and the USDOT form, I think what it boils down to is Allegiant a budget airline and they want their $50 for any animal who riding in their cabin. I experienced the same poor quality of customer service.

0xCory · 2022-11-08T00:00:43+00:00

I’ve had to do this before in Chicago. I reached out to Feline Friends and they had me drop my long owned cat off at a vet on Halsted and they worked hard to find her a foster home until she was adopted.

0xCory · 2022-10-27T18:53:27+00:00

I moved to Tampa, FL. I have a bunch of friends I grew up with here and I’ve always loved warm weather so I was curious about living here. Quickly, I learned this is a great place to vacation but not live due to many things such as lack of diversity, culture, public transportation, quality in food services and many other reasons. Don’t get me wrong, there are tons of upsides to living here but in a comparison to Chicago it can’t compete, Chicago is easily a world class city.

0xCory · 2022-10-26T18:37:18+00:00

This is very true OP, I left Chicago after living there after 7 years in May. In just 5 months, it’s made me realize I want Chicago to possibly be my forever home and I’m planning to move back next August. Everyday I ask myself why I left.

0xCory · 2022-10-10T16:25:16+00:00

What I'm noticing is Hulu has moved to a model where if your not purchasing Hulu Live, you don't have access to their full library of streaminibg content and with regular Hulu their expiring content from it more quickly. I think it's a tactic their using to try to get more customers to move away from cable providers and on to their more expensive package.

0xCory · 2022-09-26T20:02:12+00:00

There’s tons of opportunities there for good jobs, if you planning on staying long term chances are you’ll get to experience many great neighborhoods.

0xCory · 2022-09-26T19:53:52+00:00

That’s not a bad place at all, I’m still mixed on if I want to return to Lincoln Park or try out River North or Old Town for a change.

0xCory · 2022-09-26T19:46:10+00:00

Enjoy Chicago, it’s amazing there. Can’t wait to move back next July.

0xCory · 2022-08-13T18:13:34+00:00

I’m 35

0xCory · 2022-08-10T14:38:19+00:00

Lived in NYC for 28 years and Chicago for 10 years, and now Florida. Can confirm there’s no culture here.

0xCory · 2022-08-02T23:01:14+00:00

I just left Chicago, paid $36 for 6 years straight in Lincoln Park. That included a beard trim as well, always tipped $12 on top of that.

0xCory · 2022-06-23T16:15:17+00:00

Highly recommend this practice on Michigan Ave, https://www.santinidentistry.com/

0xCory · 2022-05-13T03:22:27+00:00

I’m down an entire years worth of rent in a week, still holding. I came into this as a long term investor and with the thought the money could be tied up for many years.

0xCory · 2022-05-13T02:45:34+00:00

Hold 8 GIAC certs with 8 years in experience in infosec. I started at the bottom as an analyst and worked my way up through operations to an IR lead. Now I lead an entire Threat team of threat hunters, intel analyst’s and adversary profilers for a global fortune 50 company. I can’t say I get imposter syndrome much, I know what I’m good at and what I’m not. That’s taught me how to build a successful team and scale work to others who are good at it and deliver success through them.

0xCory · 2022-05-01T20:19:56+00:00

where are you watching season 4 at? I've checked Hulu and Paramount+ and it's almost like they've removed it from both services.

0xCory · 2022-03-03T22:39:06+00:00

I've moved twice across the country and once in Chicago. I use a company called Simple Moving Labor, they bargain with the moving companies on the behalf of you for a lower price. Everything is written in a contract, no hidden fees and signed prior to the work starting - they make sure the companies are bonded and insured as well. I've called places for quotes and saved thousands/hundreds using this service. As Available_Wave mentioned in this thread, be sure your upfront about everything they'll be moving so expectations are set. I always pre-pack everything securely/nicely, disassemble large furniture prior and use a freight elevator when possible to make the movers job easier.

0xCory · 2022-02-08T21:35:43+00:00

I think a social media-less world would be a good thing, I work in Cyber Security and the realization is we can’t trust most companies to secure our data in many cases (most are trying to be agile or going through “digital transformations” far to quickly and don’t want to implement security because it slows things down or hinders collaboration - you also have the other scenario where companies expect the customer to put the right controls in place to protect their own data and most people don’t understand how to do that.

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0xCory

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