She’s Going On Vacation With Friends Who Enabled Cheating On Her Past Boyfriend

Some things to consider if your girlfriend is going on a trip with friends who encouraged past cheating.

In this video coaching newsletter I discuss an email from a viewer whose girlfriend of 7 months is going on vacation to an all inclusive resort with friends who enabled her to cheat on her last boyfriend. He’s worried she will be disloyal and cheat on him the same way she did to her previous boyfriend. My comments are in bold italics like this below in the body of his email.

Hi, I’m Coach Corey Wayne and this is my Video Coaching Newsletter in the topic of today’s Newsletter is going to be, “She’s Going On Vacation With Friends Who Enabled Cheating On Her Past Boyfriend”.

So this particular email is from a viewer. He’s a young guy, 24. He’s been with his girlfriend for seven months now. And apparently she says she wants to go on a vacation to an all inclusive resort that has alcohol, has clubs there. And apparently she’s going with the friends of hers who she admitted were there to kind of facilitate her cheating on her previous boyfriend.

So he kind of found out this after the fact because he confronted her. And, you know, initially it was, oh, she just kissed another guy, and then he pressed her on it, and then, okay, she cheated on her ex-boyfriend. And so now he’s like, I don’t really like this. And any man with common sense would think if you want to go to an all inclusive resort, which is basically for single people where there’s nightclubs, there’s alcohol, with friends that have encouraged cheating in the past, clearly support it because that’s their value system.

And you’re expected to be loyal and faithful to her and just trust that she’s a good person when she has a history of cheating. And we know she lied to him about this. So obviously, if you’re a self-respecting man, you’re going to say no to that. You’re not going to go along with it. She can go and do what she wants, but you’re just not going to be her boyfriend anymore.

Viewer Email:

Hi Coach,

I’m a 24‑year‑old male in my first serious relationship, and I’ve been with my girlfriend for about seven months. She asked me to be her boyfriend around six to seven weeks in, told me she loves me first, and often says I’m her world. I’d rate her love for me at about a 9/10. She’s introduced me to her family, she’s expressive and affectionate, and overall she seems very invested in me. Recently, though, I learned something that’s been difficult to process. She admitted that in her previous three‑year relationship, she cheated once while out clubbing. She made out with a guy and then blocked him the next day. At first, she denied it, but later confessed after I pressed her.

So we know she’ll lie to your face to avoid the truth.

The way I figured it out was because she screwed up her timelines: she told me she made out with someone last August but didn’t break up with her boyfriend until October. When I called her out, she eventually admitted she had cheated. She explained that her ex had put her down and ignored her during the last year, and that “it just happened.”

It just happened, my ass.

She broke up with him about three months later but never told him about the cheating. She insists she’s learned from her mistakes.

Once a cheater, always a cheater.

That she would never do it again, and that she would feel too guilty not to tell me if anything ever crossed a line.

Yeah, sure. What a load of bullshit that is. I wouldn’t believe her as far as I could throw her.

The issue now is that she’s planning a trip in January to Punta Cana with two of the same friends who were present when she cheated. It’s an all‑inclusive resort with clubs and alcohol, and I can’t ignore the fact that this is the same type of environment where she crossed a line before.

So my question would be, it’s like if she’s going to go to an all inclusive resort, why wouldn’t she want you to go with her? So you guys can have a romantic getaway? Why does she want to go with just these friends and not you? So if it was me and I’d be like, “No, I don’t think so. You want to go hang out with the same people that facilitated cheating? You lied to my face, told me you hadn’t cheated when you actually had, and then you finally admitted it. And I’m supposed to just trust you? It’s like. I don’t think so. You can go. But I’m not going to be your boyfriend anymore. And we’re going to break up and go our separate ways.”

I personally wouldn’t trust this girl at all, and I’d be questioning if it’s worth it to stay with her. Because she clearly doesn’t have the same value system. There’s no common sense going on in her brain going, you know, “if I was a loyal, family oriented girl, I wouldn’t be doing these things.” If she loves you, she’d be mad if you wouldn’t be willing to go with her. And she would only reluctantly go with her friends. But when you know her friends are ratchet hoes and have covered for her, and probably encouraged her to cheat and they want her to go, it’s like, I don’t think so. I wouldn’t want to be a part of that. I wouldn’t even want to keep dating a girl after this confession. Because, again, there’s no common sense. There’s no, “Uh. Well, all my boyfriends have a problem.” It’s like. Hello?

The issue now is that she’s planning a trip in January to Punta Cana with two of the same friends who were present when she cheated. It’s an all‑inclusive resort with clubs and alcohol, and I can’t ignore the fact that this is the same type of environment where she crossed a line before. Part of me feels I should set a firm boundary, such as telling her that if she goes on this trip, I can’t continue the relationship.

That’s exactly what I would do, dude.

Another part of me worries that this would come across as controlling, even though my intent is to protect myself and ensure loyalty.

Yeah, again, I would not agree to it. She demands she wanted you to be loyal to her, and yet she wants to basically go act like a single person. And, you know, because the last time. “Oh, it just kind of happened.” And so what, she goes there, and then she gets a little too drunk. “Oh, it just happened. Some other dude ended up inside of me.” It’s like, yeah, I don’t think so. If she says it’s controlling behavior, just say, “No. It’s called loyalty. It’s called self self-respect. It’s called respect for our relationship. And you clearly have none. If you think that this is a good idea when you already have a history of cheating and lying.” So if it was me, I’d be like, “Well, this is where we part ways, sweetheart. You go on your trip, have a great time with your fucking dirtbag friends. But I’m not going to be involved.”

From an outsider’s perspective, she has a complicated past with a toxic ex‑boyfriend.

So we know her decision making is not very good.

But she’s close with her family and seems genuinely invested in me now.

Just because she’s close to their family doesn’t mean she was raised properly and her dad did a good job. That’s the way I’d be looking at it. So if she had a good father that had a shit together and was the man of the house and respected her, he would have intervened in that relationship wouldn’t have been an issue. She would have never gotten that far down the road with that dude. But she clearly doesn’t have the same values as you, and all we have to do is look at her actions. That’s what tells us everything about her.

She goes there and sleeps with a guy and goes, oh, it just kind of happened. She let it happen. She put herself in that position. So that shows she has poor judgment and she doesn’t really value loyalty, commitment, family. So she’s a fuck buddy, friends with benefits, sex playmate. I would be exiting this relationship. If it was me, I’d be out. Just the fact that she brings this up and says, “Oh, by the way, I’m going to go to this resort.” It’s like, “Hey, that’s awesome. But I’m not going to be your boyfriend anymore. Especially after what you told me and the fact you lied about it. I’m not down.”

I trust her to a degree, but I’m struggling with whether her words will translate into consistent action.

Well, if all we have to go by is her actions in the past, we know she’s a liar and a cheater. And we know she lies to your face. So I wouldn’t believe anything she says at this point. Because, you know, love cannot exist where there is no trust. And she screwed the pooch.

My question is, should I break up now to avoid future pain, say nothing and hope for the best, or set a clear boundary and see how she responds?

If it was me knowing what I know now, it’s like I would exit the relationship and just move on, because she does not share your value system. I mean, again, it didn’t even dawn on her to think, well. It’s not a good look. But again, she doesn’t have the same value system that’s why she thinks this is fine.

I want to build a relationship based on honesty and respect.

Well, she’s not honest. She lied to you. She lied to you about the cheating and then later admitted it when you pressed her.

But I also want to protect my self‑respect and long‑term goals.

So at the end of the day, my man, there’s not a lot you can do with this. That’s the way she is. This is how her family raised her. Again, if she’s raised by a family, can you imagine a guy who’s family oriented and his daughter says, yeah, I’m going to go to this exclusive resort with a bunch of single people. You know, they got a nude and a prude side, and there’s clubs and alcohol. And the last time she went there, she’s going with people that lie and cheat. Because whoever she’s hanging out with probably is cheating on their significant others. So it’s like, again, if it was a family oriented father, he’d be like, are you out of your fucking mind? If you go there and do that, you’re not going to be my daughter anymore.

It’s like, I don’t think so. Nobody’s going to encourage it. No self-respecting man is going to be down. But it’s your life. You can do what you want. You can tell her, “You know. No, you’re not going. That’s not okay. And number two. You’re like, you’re not going to hang out with those friends anymore. If those friends were there and supported, you cheating. I don’t want anything to do with them, and I don’t want you to have anything to do with them. And if you think it’s a good idea to keep people like that in your life, we don’t share the same value system. And therefore I’m not going to stay with you. I’m leaving. I’m out. Go have fun. Go fuck who you want.” Oh, it just happened. Can’t turn a hoe into a housewife, my man. And unfortunately, this girl doesn’t share your value system. But it’s your life.

You do what you want. Me personally, I’d be tapping out and riding off into the sunset. But if you want to set the boundary and see if she respects it, you know, if you say, “You’re not going”, and then she’s like, “Well, I’m going anyways.” It’s like, “Great, I won’t be here when you come back.” So you can’t, this is not, you can’t make good wine from bad grapes. There’s just really nothing that’s fixable here. And it’s unfortunate, but you’re young. This is why you date to vet for character. And now you found out that your supposed girlfriend of seven months. Is a hoe bag, a liar and a cheater, and you’re just not going to fix it. Her dad screwed her up.

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