My Ex Is Dating My Friend, But Hits On Me. What Should I Do?

Coach Corey Wayne
13 min readSep 14, 2023

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Photo by iStock/vgajic

Some things to consider if your ex is dating a friend and she hits on you even though you have a girlfriend.

In this video coaching newsletter I discuss an email from a viewer who says his ex girlfriend from over 2 years ago is now dating a friend of his. He and his new girlfriend went on a double date with his friend and his ex. It seemed to go well and everyone had a good time.

However, Immediately after their double date, his ex reached out directly and made several attempts to go on a date with him alone despite the fact she is dating his friend and he has a new girlfriend. My comments are in bold italics like this below in the body of his email.

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Well, this is an interesting conundrum that has happened. So this particular guy got rejected. He got dumped by his ex a couple of years ago and he says he had blocked her on everything and she moved away, and kind of put the past in the rear view mirror.

He’s in a new relationship with a girl he really likes. He’s really in love with her. They’re going really great. Then one of his, he says, is a good friend or a close friend, got in touch and says, “Oh, by the way, I’m dating your ex,” and he thought about it and he said he was looking at another video of mine, because I have good relationships with most of my ex-girlfriends, especially when you’re the one that does the dumping and you can be on good terms with people. He was like, “You know what? I’m really happy in this relationship. I’m not interested in getting back together with her, and my friend Bob is dating her,” because he came to him and he’s like, “I kind of been dating your ex,” and he’s like, “Hey, let’s go out on a double date. That’d be fun.”

So they go out on a double date, and it actually was a lot of fun. Everybody had had a good time, but afterwards she started hitting on him directly. So it’s pretty interesting what happened.

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Viewer’s Email:

Dear Coach Corey,

I hope you are well, I emailed you my success story a while back and there’s been a few updates which may interest your subscribers and video viewers.

My ex Jessica, who dumped me 2 years ago, has now moved back to town after living abroad for a long time. I was crushed when we broke up, but dived into Your Book and read it over 15 times, applied myself and moved on. I am now doing great in my career. I also have a beautiful girlfriend who is in love with me, and I am in love with her.

And they all lived happily ever after.

I am also in great shape with hiking, running, cycling, swimming and weightlifting regularly. I have had a spiritual awakening and practice meditation daily, which makes me more aware of living in the present moment. It was a hard journey with many false starts, but I did it.

Well, congratulations on your success.

Long story short, my ex has started dating Bob, a close friend of mine who is kind of a fuck-up, but very charismatic and a great guy. He came to me a little embarrassed and told me about it. My response, inspired by one of your videos, was “Hey, I love you both, you are great people and I’m happy for you.”

Photo by iStock/EXTREME-PHOTOGRAPHER

I had something similar happen. Maybe he’s referring to the story I was talking about my ex-wife, this is over 20 years ago at this point. So obviously my ex-wife and I, we split up. I was 26 years old and we were friends for several years. Then she moved back to South Florida, and I hadn’t heard from her in years. This was about, I think it was like 2001, maybe. In 2002, I was dating my girlfriend that had the little girl, the daughter at the time, who was like five-and-a-half, six years old, who is now closing in on 30 years old and has a couple kids of her own, which I still can’t believe that. It seems like yesterday. What the fuck?

Anyways, I’m very happy in a new relationship, I’m totally in love with this girl and getting to be a part-time dad. It was just magical. It was beautiful. I was very happy. It was like at that point in my life, I was happier than I ever been. So one of my high school buddies, unbeknownst to me, was dating my ex-wife for like a year, and one of my other close friends was down in South Florida visiting, and he’s like, “Hey, you want to get together and go hang out with so-and-so?” I was like, “Sure, I haven’t seen him in a few years. What the hell is he doing? What’s he up to?” He’s like, “Well, he’s dating so-and-so.” I was like, “Really? How long have they been dating?” He’s like, “A little over a year, but he was afraid to tell you because he thought you’d be mad.” I was like, “What? Well, I left her. I want her to be happy. She’s a great girl. I love both of them. We should get together and hang out.”

So we ended up getting together. We met actually at, what was it, Solid Gold? I think it was Solid Gold, which was a titty bar. So my buddy and I, because obviously my girlfriend is back in Orlando and his wife was out of town with his kids visiting family up north. So I was like, “I would love to see her,” and at that point, it had probably been five or six years at least since I’d seen her and my buddy. I hadn’t seen him in like a year-and-a-half, two years. Then it kind of made sense why I hadn’t heard from him because he was afraid that if I found out he was dating my ex-wife, that I’d want to beat his ass or something. I was like, “Let’s get together.”

Photo by iStock/monkeybusinessimages

So we hung out at the titty bar, laughed, caught up, had a good time. Everybody got some lap dances. Then we went to Denny’s afterwards. I haven’t seen her since, but I know they dated a year or two after that, and then they split up and went their separate ways. Now he’s married and very happy. So I was like, “No big deal.” So I assume maybe that was the story that kind of inspired this.

With that in mind, that was the same kind of mindset, because it was great to hear that they were happy. Like, I love both of them. I was excited that they were dating and enjoying each other. Didn’t ultimately work out, but it was cool after five or six years and I hadn’t seen her or talked to her to hang out like that. So back to our regularly scheduled email. So with that same idea and vibe in mind, this is his conversation to his friend.

“Jessica and I broke up years ago. I’ve moved on and she has too. It’s great that you are together. Tell you what, why don’t we all get together sometime?” We agreed to do a double date at a favorite restaurant of mine the following week. My ex and I had barely spoken since the breakup, and I assumed it would be awkward since I had blocked her on all social media (This was before I read Your Book).

Keep in mind, it’s going back a couple of years. He ain’t spoken to her since, as far as I know.

However, I was proved wrong as the evening was very pleasant and conversation flowed freely.

Photo by iStock/monkeybusinessimages

Well again, I was cool with getting together with my ex-wife because we parted on good terms and I was happy to see my buddy again and two people I love are now dating. I was like, “This is awesome! Good for them!”

I love it when people are happy. It’s just one of the many reasons why I became a coach. I rejoice in the success of other people. It makes all the struggle and all the shit that I went through to learn these things worth it.

My ex did not speak much, mainly Bob, my current girlfriend and myself, were mainly in the conversation. Jessica did interject from time to time, but it seemed like mainly she was just observing me and my current girlfriend.

Interesting… Fascinating…

I remember feeling relieved that the evening went well and that we could all move on as friends with no disruption to the friend group.

After the meal, we all hugged each other and went out dancing. I’m kind of a novice dancer but my ex’s new partner is pretty skilled, and he was all over the dance floor dancing with many partners. My girlfriend and I just danced together, with a few exceptions. Also, we are both musicians, so we were mainly interested in listening to the excellent band.

As the evening progressed, Bob got more and more drunk and more and more over the top with his dancing, and then announced that he and Jessica were going back to his place to do psychedelics.

Photo by iStock/South_agency

Maybe magic mushrooms, or maybe a little of other things. I don’t know if I should mention it just because YouTube, the pimp hand and the censorship, so I probably won’t say those things. Micro-dosing some interesting products.

Bob has always been an enthusiastic drinker and recreational drug user. He invited us but we declined. My girlfriend and I went home, put a movie on and ended up doing the indoor Olympics at our shared house. I woke up the next morning feeling that I had turned a page in my life. I was able to interact with my ex freely and without awkwardness — Being happy for her and her new man.

However, a few days later, I got a text from Jessica. It said this.

Let me get my girl voice ready…

“Hey…”

A big shock. A woman’s favorite line, “Hey.” It’s just a h-e-y.

“…It was so great to see you the other day. You look so happy, and your new girlfriend is beautiful. I miss the days before we were dating when we used to go hiking and on other adventures together. Let me know if you’d like to pick that up again.”

So she’s basically saying, “Hey, I’m totally down with you cheating on your girlfriend and I’m happy to cheat on my boyfriend, which obviously you’re a great friend, but we won’t tell anybody.” Not that she said that, but it’s kind of the vibe. She’s being pretty bold here.

Photo by iStock/Antonio_Diaz

I found this to be wildly inappropriate since one of my ex and I’s hiking dates had ended with us having sex in a river…

Naughty! So animalistic! The call of the wild! Were you howling at the moon? Do you know there’s a mouse, I can’t think of the name of it. It actually howls at the moon and like, eats snakes or something? I talked about this in a video a few years ago. I did one of our Instagram images. I can’t think of the name of the mouse. Somebody can maybe post it in the comments, but it’s kind of funny that the mouse literally howls at the moon.

…And I did not know what to say. I showed the text to my girlfriend and we both agreed on this response.

“Hey, we’d love to go for a hike with you and Bob whenever you are free,” and signed off with both our names. There was no response, then a few days later, Jessica messaged me on Telegram…

Ooh, a little more James Bond-like.

…An app we used to use to communicate years ago and which I had forgotten was even on my phone since I never use it now. It said, “Hey…”

Favorite line again…

“…I hope I wasn’t inappropriate with that text I sent. I just want you two to be happy, but if you ever want to go on a one-on-one hike, just let me know.” I immediately showed this message to my girlfriend who thinks I should tell Bob at once.

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I am unsure what to do now to protect my friendship with Bob. Should I tell him about the text?

Bob

Well, that really depends on how good of a friend Bob really is. The right thing to do, the honest thing to do, is to send him screenshots of this, call him up and say, “Hey man, I hate to tell you this, I haven’t talked to Jessica in years and we were genuinely happy that you guys got together, but your girlfriend is hitting on me, dude.”

“On top of that, it’s obvious that she was hoping that I was willing to cheat on my girlfriend because it’s pretty obvious she was willing to cheat on you to have another shot at yours truly. So I don’t think I’m going to be wanting to hang out. My girlfriend and I aren’t going to want to be hanging out and doing double dates anymore because it just wouldn’t be appropriate to be going on double dates with a woman that’s basically trying to rip me off from my current girlfriend, out of respect for my relationship because I love my girlfriend and she’s great.”

This is obviously disloyal behavior. This ex of his has terrible character. I mean, what a messy situation, but I can understand, maybe she’s thinking she’s remorseful because women like you more if other women also like you. The fact that you’ve moved on, you’re more fit, you’re in shape, you’re happier, you’ve got a pretty girlfriend, now her attraction has gone up. So she’s shooting her shot with you, but I don’t remember the context. I looked through the emails and I couldn’t find any previous emails from this guy or any newsletters where I had discussed. So I’m not sure. Maybe he used a different email address and that’s why I couldn’t find it.

Photo by iStock/FabrikaCr

So I don’t know what the history was with the two of them or if he even had sent it in before, but when you see this kind of behavior, you just avoid hanging out with them. I would not be doing any more double dates with them because this is just inappropriate. In other words, their first response was letting the ex know that him and his girlfriend were aware of what she had said, but despite that, she then goes to Telegram thinking that she’s going to be able to talk to the emailer directly and again, tries to fly under the radar.

The right thing to do is to tell your friend Bob. If more than likely, because we all got guy friends like this, probably Bob ain’t going to listen anyways. He’ll talk to her, they’ll talk it out and she’ll give him some story or excuse, and if he’s really thirsty and really into her, he’ll probably forgive her and assume he can trust her until he eventually gets burned down the road and finds out she’s cheating on him with somebody else.

Me personally, when you see that kind of behavior, yeah, I would not, because whenever you tolerate somebody with low character like this in your life, you’re just inviting them to do it again. On top of that, like attracts like. If you tolerate a low character person, who is a low character person going to bring into your life? More low character people. Where intention goes, energy flows. Whatever you observe, you participate in.

Photo by iStock/SIphotography

I personally would not be participating with the ex Jessica in any way. You gave her the benefit of the doubt. It was a nice thing to do, but now you really got to see probably a different side of her that I don’t know that this guy ever got to saw when he was dating her.

So I would definitely tell Bob, if he’s a good friend. If he’s somebody you don’t like and he’s an ass and he deserves it, well you know, that’s on him. You can do whatever you want. If he was a good friend, like it was my buddy and something like that was happening, like he was dating somebody else and I was in the same shoes, I would definitely tell him, because I’ve known this dude since I was in high school, so of course I’m going to tell him. It’s your choice.

I wouldn’t associate with her anyway because again, you’ll be inviting more people with low integrity into your life and potentially your relationship, and it’s just not good. You and your girl are on solid ground. You got to be very careful about who you let into your inner circle, and this girl does not belong.

So, if you’ve got a question or a challenge and you’d like to get my help, go to UnderstandingRelationships.com, click the Products tab at the top of your screen and book a coaching session with yours truly. Until next time, I will talk to you soon.

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Coach Corey Wayne

Life & Peak Performance Coach. I Teach Self-Reliance. Subscribe To My Newsletter To Read My eBooks “3% Man” & “Mastering Yourself” Free: http://bit.ly/CCWeBooks