I don’t know how to break up with my girlfriend

Me (Josh, 26m) and my girlfriend (Penny, 25f) have been together since we were around 17 years old. We met in high school and had an instant connection. I mean the type that has you opening up and spilling your darkest secrets just 2 weeks getting to know each other. We both had rough childhoods and maybe that’s what bonded us together. She dumped me maybe 6 months into us dating because she was just going through a lot and couldn’t handle being in a relationship. It hurt me a lot but I cared about her and just wanted her to be happy. We spent that summer before our senior year of high school as friends and I gave her the time and space she needed. When school started back up that fall we began seeing each other again and going on dates but I didn’t want her to feel pressured or rushed so I didn’t ask her to be my girlfriend until after we graduated. We did a lot of couple things during that time and we both knew we had deep feelings for each other. It was like things didn’t really need to be said for them to be understood.

After graduating we both went to our community college and started seeing each other more and spending nights together since she had more freedom after turning 18. It was maybe a year into us seriously dating that I caught her cheating on me for the first time. When she was sleeping, I went through her phone and saw she had been messaging Austin (her best friend’s boyfriend) behind Emma’s (her best friend) back. I was honestly shocked and didn’t know how to respond at first. I just put her phone back and went to sleep in the other room. The next morning when she woke up she asked what I was doing in the other room but I could tell by her expression that she knew I caught her. She immediately started telling me that she was sorry and that it was just a mistake. I, of course, asked for all the details.

She told me, the summer before senior year when we were broken up, she ran into Austin at a party and they hooked up. She said during that time Emma and Austin were not together otherwise she would’ve never done it. I asked what she meant by “it”. She told me that they went to his truck and they made out and eventually gave each other oral. She insisted that there was no penetration. I asked her what Emma thought about all of this and she told me that Emma had no clue about their fling which was shocking because Emma and Austin reconciled during our senior year of high school as well. I did the right thing and I told Emma about Austin and Penny but they both blocked me and remained together.

I did end up forgiving Penny because she was extremely apologetic and seemed genuinely ashamed of her actions. It took a lot of effort but we eventually did become happy and the trust came back.

Fast forward 2025.

This past April, Penny went out to the bars for a girls night out which is something I was comfortable with. I decided to stay in have some drinks at home while I watched some movies. We had been texting each other the whole night and keeping each other updated with whatever we were doing. Around midnight she wasn’t replying at quickly as before but I told myself she was probably just having a good time and not to worry. I did have a small feeling in my stomach telling me something was wrong but I told myself everything was fine. After not hearing from her I decided to call around 12:45am. After a few missed calls she finally picked up and told me her friend needed help because they got a flat so she’s going to have to drive them home. My stomach dropped and I immediately knew she was lying. Besides her story making no sense I could just tell by her voice. I hung up the phone and texted her that if she is on any bullshit she will be coming home to an empty house. I stayed until about 4am before I packed all my things and went to my parent’s house.

The next morning she called me and told me she was at her cousins house bc it was closer than ours to her friend’s house and she didn’t want to drive all the home so late. I asked simply if she cheated on me and she kept insisting no and that it was just a crazy night and things just kept going wrong. I knew she was lying to me but I had no proof and I didn’t want to be angry at her for helping a friend if that’s really what happened. I told her to come home and we could talk more. When we were in person I could see how badly she wanted me to believe her. She looked very guilty and maybe that was enough for me to forgive her but she didn’t confess to cheating. I stayed with her.

Fast forward to August of this year. We had been drinking one night and the memory came back. I’m never one to rehash things once they were settled but this still felt so unsettled to me. I brought it up and like the skilled liar she is, she stuck to her story. I couldn’t get her to break. At this point all I really wanted from her was the truth. I remember that night I spent time praying that the truth would reveal itself to me. The next morning I woke up to pee and felt the most excruciating pain I had ever felt before. I told penny that I was going to an urgent care because i had a stomach bug but I really was going to get std tested.

It came back that it was just a UTI. I was going crazy at this point. This is where I may be wrong.

When I got home I told her Penny that I tested positive for an std and that she needed to fess up about what really happened that night in April. She immediately started crying and saying the doctor was trying to ruin our relationship and that there was no possible way she could’ve given me an std. at this point I knew just by her reaction that she was lying. She started deflecting and talking about our future and how we have plans and dreams together and she even asked for us to get married.

Eventually I started screaming and throwing things just begging her to be honest and to just do the right thing. I guess she saw that there was no use to lying. She finally confessed and told me that night she started talking to a guy at the bar and hooked up with him in her car. She said he gave her oral but that there was no sex. It reminded me instantly of the Emma and Austin situation from high school. By now I knew I couldn’t trust anything she said but I hounded her anyway.

She confessed to sleeping with Austin. After nearly 10 years she finally confessed to that lie. How could I ever build a future with someone like this? She’s sticking to her story that it was just oral with this club guy but I believed that lie once before and the only reason I didn’t care about Austin was because we were not dating during that time.

After she told me the truth about the night in April I of course broke up with her, or tried to at least. She tried to kill herself by crashing her car. Now look I’m not heartless or evil so I couldn’t just leave her in this horrible emotional state. I told her I’d try to work on things and rebuilding trust but it’s been 4 months and I still feel disgusted. Of course I love Penny and we have a strong connection but now that I know more there’s no way I could possibly have a serious relationship with her. I feel bad like I’m leading her on but I just don’t want her to die. I know she’s evil and a disgusting person for cheating and manipulating me but I can’t just watch her life fall apart.

After our break up, most of our friends cut her off. All of my family removed her from social media. Her mom went off on me. She said what her daughter did was wrong but she doesn’t deserve for everyone to hate her and that people make mistakes. I told her I didn’t want anyone to hate her and that this isn’t something I wanted to happen but that relationship is severed now too.

Anyway I guess what I’m asking is how can I break up with her without feeling guilty? I know she did wrong to me but I hate seeing her so down. I do love her but I’m not in love with her any more. It still hurts to cause her pain. Someone help me please!