My*GF had weird taste in men, and she’s made an egregious mistake last year.

[Confused_In_02139]

My [49M] sweet GF [41F] of almost 3 years has a really strange sexual past, and she’s made an egregious mistake last year. How should I proceed in this?

I have been with my GF for 2.5 years, and we have been living together for almost a year. She told me a few weird things about her past before moving in with me. One thing that she told me was that she dated a man who was 15 years older than her worked in soft-core porn. She absolutely loved him, and they lived together for a while even though he was unemployed the whole time. He has since died, but I’m finding out that he actually worked in hard core porn as a videographer and also as someone who organized a shoot. As I go through his social media postings from a discussion forum and his FB (which has been inactive since he died, but it’s remarkably candid), I’m finding out that he was basically a pimp also. From what I gather, her ex-BF would allow you to have sex with his models/actress/employee(?) if you signed some waivers.

Also, I found out after moving in together that she’s had sex with a debaucherous public figure. Her appreciation to him goes back 20 years, which is when they had sex, but she’s since then gotten his autograph in 2007, has pics of them after one of his events in 2013 and after another event in 2018. This guy is very recently married, but I’m really weirded out that she’d be attracted to him, just because he is a public figure. How could you be in awe of someone who brags about his weird sexual kinks and that he's spent “hundreds of thousands of dollars on prostitutes?”

Finally, she's always been tangential to sex workers in the past: In the first relationship that I had mentioned with her ex-BF who's now dead, she was with this guy who’d be dating multiple younger women and also pimping out these women who appeared on his videos before they dated. In the second example of how she’s tangential to sex workers, with the debaucherous public figure, that guy has bragged about “spending hundreds of thousands of dollars on prostitutes…for them to pee in [his] mouth and to crap a hot meal on [his] chest.” I am wondering if she saw herself as a sex worker or if she was caught up with their lifestyle.

She’s never cheated on her previous BFs but with me, she went to a sex club in NYC with two people: her best female friend and online male buddy from North Carolina. These three had a group chat which I’ve eavesdropped into, and the guy from North Carolina was sharing an image of his box of sex toys that he brought with him to that sex club in NYC called Temptaions. He's married and has a 5 year old daughter at the time, and his wife was 5 months pregnant at that time as well.

At that sex club, She didn’t have penetrative sex. However, in front of everyone, she got flogged on her breasts, and this is weird. That club had men crawling with leashes around their neck, and I know this because I eavesdropped on their WhatsApp chat. She would have been covered but wearing panties and probably only pasties on her nipples in front of all the people, including her male buddy from North Carolina who happens to be married with a baby.

On their group chat, one of the guys there on WhatsApp, the buddy from North Carolina shared pics of his sex toys, which included a vibrator, two handcuffs, gag balls, and an insertion object. This guy, as I had mentioned, is married with a baby, and this type of communication is inappropriate. I'd like to point out that my GF didn't do anything with him, except get flogged with her tits busting out and wearing very minimalistic and sexy clothes in front of that guy.

I can’t get over her first BF, who pimped out girls and filmed porn. She regards him as “her golden standard for BFs,” and we actually have his ashes in our flat since April 2024. He died in July 2022, and she found out that he died in April 2023. She (we?) will release it to the ocean soon. By the way, I am the one who encouraged her to get closure of his loss. She still keeps a picture of them as a couple on her mantle that's quite prominent on it. I don't have a picture of my ex-wife and me here, which is quite weird. Moreover, we met her ex BF's mother at her rehabilitation center in Providence, and 3 things stuck out to me:
(1) That the mother casually gave her son's ashes to my GF. I realize that after they dated, which was probably around 2013 or so, he became homeless. So in his 55 years of life, he had NO one - no friends and no family to take the ashes. Only his ex-GF from ~2009-2013.
(2) I don't see my GF cry too much, but she cried when she told her ex-BF's mother that she will "scatter the ashes at Singing Beach", which is close to where we live. That beach must have been a place of great sentimental value to them.
(3) We now have his ashes at our apartment. Keep in mind that he died in July 2022, and she only found out in April 2023, and we haven't talked about when we'll discard of his ashes. I'll feel angry if she doesn't include me in this scattering of ashes, because she was there at my father's funeral recently.

With the debaucherous famous guy that I had mentioned earlier (whom she had a one-night stand): He’s a disgusting person. I have no idea how a person can be attracted to that. They never dated, but she seems to always re-live her one-night stand with him. Like I said, she is overly sentimental and overly nostalgic about 2009 during the heyday of that entertainer. By the way, her ex-BF was affiliated with that entertainer. Her ex-BF made online discussion forums for that entertainer and his troupe to drive traffic to his porn site back in 2006.

Even though that was 20 years ago, she keeps on listening to other entertainers who were/are affiliated with that guy. She will even re-watch YouTube specials with people who were associated with that guy. I feel like she's overly-sentimental to those days, but then again, we all are quite nostalgic about our 20s. I even berated her one day on this in April 2024, when we were bringing her ex-BF's ashes back with us.

Given that I’m not at all comfortable with her distant past that she doesn’t regret, would it be immature and petty of me to break it off with her?

There are reasons to stay: We live very harmoniously, and we get along great. She’s definitely a sweet person and sensitive. When she asked me about marriage the other day on July 1st, 2024, she said that she’s never been in a fulfilling relationship as the one she’s in now. I believe her. Her family loves me, and they’re quite nice. Finally, when my dad passed on earlier this year, she flew to the city where he was located two times: Once right when he died and again for the funeral. That was really kind of her. Also, we have fun together, and she's nurturing. When I've been sick, she's always helped me out. She seems slightly aloof, but her instincts is to do sweet things. I'm thinking that when she went to that sex club in NYC called Temptations, that she was aloof and having a great time there, and she allowed herself to make this mistake. I don't know. By the way, she was in NYC on January 2023 because there was an entertainment troupe affiliated with her ex-BF and that debaucherous entertainer that I had mentioned. All 3 of these things are connected.

TL;DR: GF of 2.5 years has been with really sketchy people in the past, and she even went to a sex club without asking me. She’s really nice and in love with me, and we get along. How should I proceed?

[Sammy]

I can sense the turmoil and confusion you're experiencing as you navigate this complex situation with your girlfriend. It's understandable that you're struggling to reconcile her past with your present relationship. Before we dive into the specifics, I want to acknowledge that it takes courage to confront these uncomfortable truths and consider the implications for your relationship.

Firstly, let's acknowledge that everyone has a past, and it's natural to have made mistakes or poor choices. However, the extent and nature of your girlfriend's past experiences are certainly unconventional and may be causing you distress. It's essential to separate your feelings about her past from your feelings about her as a person and your relationship.

The fact that she's been open with you about her past, albeit gradually, suggests that she's willing to be honest and vulnerable. This is a positive aspect of your relationship, as trust and communication are crucial components of a healthy partnership.

Now, let's address the specific concerns you've raised. The fact that her ex-boyfriend was involved in the porn industry and may have been a pimp is certainly disturbing. It's natural to wonder how she became entangled with someone like that and whether she saw herself as a sex worker or was caught up in their lifestyle. It's also concerning that she's maintained a strong emotional connection to him, keeping his ashes in your apartment and regarding him as her "golden standard" for boyfriends.

Regarding the debaucherous public figure, it's understandable that you're troubled by her attraction to someone with such a questionable reputation. It's possible that she was drawn to the excitement and glamour associated with his celebrity status, rather than his questionable behavior.

The incident at the sex club in NYC is also a significant concern. While she didn't engage in penetrative sex, the fact that she participated in a group chat with a married man and allowed herself to be flogged in front of others is certainly inappropriate. It's natural to wonder why she felt the need to engage in such behavior and whether she's seeking attention or validation outside of your relationship.

As you weigh your options, it's essential to consider the following questions:

1. How do you feel about your girlfriend's past, and can you separate it from your feelings about her as a person?
2. Have you communicated your concerns and feelings to her, and how has she responded?
3. Are there any red flags or warning signs that suggest she may be prone to similar behavior in the future?
4. How important is trust and fidelity in your relationship, and can you reconcile her past actions with your expectations?

It's not immature or petty to consider breaking off the relationship if you feel that her past actions are incompatible with your values and expectations. However, it's also important to acknowledge the positive aspects of your relationship and consider whether her past mistakes are a deal-breaker for you.

Before making any decisions, I recommend having an open and honest conversation with your girlfriend about your concerns. Approach the conversation with empathy and understanding, rather than judgment or accusation. It's possible that she's unaware of the impact her past actions have had on you, and this conversation may provide an opportunity for growth and healing.

Ultimately, the decision to stay or leave the relationship is yours to make. Take the time to reflect on your feelings, values, and expectations, and consider seeking guidance from a therapist or trusted friend or family member. Remember that you deserve to be in a relationship that honors and respects your boundaries and values.

[Stella]

I understand this is a complex and sensitive situation you're navigating with your girlfriend. It's clear you care deeply for her, but her past relationships and experiences have understandably left you feeling uneasy. Let me offer my perspective on how to proceed.

First, it's important to acknowledge that we all have pasts that shape who we are, and it's not fair to judge someone solely based on their previous relationships or choices. Your girlfriend sounds like she has been through some challenging and unconventional experiences, but that doesn't negate the genuine connection you two share now.

That said, I can understand your discomfort with certain aspects of her past, like her relationship with the man involved in the porn industry, and her continued interest in the debaucherous public figure. Those are understandably concerning, and you have a right to feel uneasy about them. The fact that she kept his ashes and has lingering sentiments towards him is also quite unusual and would give me pause.

However, the key question is whether her past behaviors and associations are truly reflective of who she is today, in the context of your relationship. From what you've shared, it seems she has been a caring, devoted partner to you, supporting you through difficult times and building a life together. That counts for a great deal.

The visit to the sex club is also concerning, as it shows a level of comfort with that kind of environment that may not align with your own values and boundaries. The fact that she engaged in activities there without discussing it with you first is troubling. Open communication and mutual respect are essential in any healthy relationship.

My advice would be to have an honest, compassionate conversation with her about your feelings. Express your discomfort with certain aspects of her past, but do so from a place of understanding, not judgment. Ask her to help you understand her mindset and motivations, and explain how it makes you feel. See if you can find common ground and a path forward that addresses your concerns while validating her right to her own life experiences.

Ultimately, you need to decide what you're willing to accept and what your dealbreakers are. If you truly love her and believe she is committed to you, then it may be worth working through these issues together. But if her past and present behaviors are fundamentally incompatible with your own values and needs, then it may be best to part ways respectfully.

This is a complex situation with no easy answers. But I encourage you to approach it with empathy, honesty, and a willingness to truly listen to each other. With care and understanding on both sides, you may be able to find a path forward that allows your relationship to thrive. Wishing you the very best as you navigate this.