Dating My Ex’s Sister. Mission Impossible?

Navigating dating the sister of your ex-girlfriend.

In this video coaching newsletter I discuss an email from a viewer who was engaged and dated his ex roommate for about five years. He realized he was really into her sister and not so much her. Eventually they had the hard conversations and broke up. four years later he started dating her sister after she reached out. Things were great for about a month. Then his ex torpedoed the romance and he got ghosted.

He wonders if there’s anything he can do now. My comments are in bold italics like this below in the body of his email.

Well, I got an email from a viewer who has decided to take on a sticky task and a little, you could say, drama. This guy basically, I assume it was in college, he met this woman. It was his roommate. At some point, they started dating. It was kind of a thing of convenience. He said his father passed away unexpectedly, and she was kind of his security blanket or emotional support human, but deep down, it never felt right. As a matter of fact, he always had the hots for her sister.

So anyways, after about five years of being together, they eventually got engaged. He realized, especially as he grew up, that he just couldn’t continue lying to himself. So eventually he and her had the hard conversations about the true nature of their relationship and his feelings. He basically says he came home one day and she was already packing her stuff up to move.

So fast forward four years and this girl’s sister reaches out to him and they start dating. At first everybody, was encouraging, including his ex, but then his ex couldn’t deal with the fact that he basically chose her sister over her and she pressured her sister. Blood is thicker than water, the whole nine yards. So the sister basically ghosted this guy.

I suspect he displayed a bunch of unattractive behavior towards the end, because at the end of the day, women don’t dump men they’re in love with. They dump men they’ve lost respect and attraction for. If he’s getting ghosted and continuing to try to contact her, that just sounds like the wheels came off the wagon at the end there. So he’s wondering if reaching out and vomiting his feelings or trying to contact his sister once again, even though she’s ghosted him, is going to make a difference at this point.

So let’s go through his email.

Viewer Email:

Hi Coach Corey Wayne!

First off, I just wanna say you are the freaking man! You have helped me so much in my journey with women. You’re like that cool older brother I never had. So thank you. 

My question is related to something I feel like was in a Seinfeld episode, the one where Jerry attempts to date the roommate of a woman he is currently seeing.

It’s like stuff like that has pretty much happened to every dude. Start dating a girl you like, her sister, or cousin or whatever. It happens, especially when you’re younger, because when you’re younger, you’re less inclined to stand up for yourself and what you want. You kind of think, “Well, I don’t want to rock the boat. I don’t want to make things difficult for anybody. So I’ll just go along to get along.” As you get older and you get burned and you get tired of putting your needs last, eventually you grow out of that like I did.

Coach, I think this one is even more impossible. Dating the SISTER of a woman who I was ENGAGED to!

Well, obviously you like a challenge.

Coach, like most guys in their twenties, I didn’t know jack shit about dating, love, women. I fell in “love” with a woman who was my housemate at the time. I didn’t realize that my love for her was more of a sisterly/friendship love (I had never been in a long-term relationship at this point. Just a few flings in college. So didn’t really know the difference).

Yep. Been there, done that, got the t-shirt. Especially if you’re like a late bloomer like I was, you don’t have a lot of experience, and then you finally come across a girl that seems like no matter what you do, she just thinks you’re the shit, and that’s where indifference really pays off. You do enough to maintain the relationship, but not enough to where you are all over the ice and turn her off with unattractive behavior. So that’s why every guy finds it’s much easier to date women that they’re either not that into or have mediocre interest in, but the girls we really like, we have a really hard time acting and behaving the same way and keeping those girls interested and attracted. It’s like they always seem to just slip through our fingers.

I remember when I was in my 20s, I didn’t understand why that was. How things would start off great for a few weeks, and then three, four weeks later, you’d get the dreaded friend-zone speech or, “There’s something missing. There’s no chemistry. There’s no spark.” The reality is that we tend to treat the girls we really, really like, different than the ones we could take it or leave it. The reality is, we got to treat them all the same way because indifference is the difference that actually makes the difference.

I also didn’t realize that the feelings I had for her sister were the real deal. Over the next year or two, as I dated “the roommate,” it became clear that I wasn’t attracted to her on that same passionate/soul level that I was to “the sister.” I wrestled with this for a long time, because I generally liked/loved “the roommate,” and I think felt guilty about the feelings I had for her sister.

Yeah, there’s nothing worse than being in a relationship with a girl, then especially when you’re younger and then you meet somebody else, maybe somebody that’s related or a friend of the girl you’re dating and you think, “Man, why am I more attracted to the friend or the cousin or the sister than the girl I’ve been with for a year or two? That doesn’t make any sense.” Then that just eats at you and you wonder like, “Why is that? Why is that happening?” I believe because those people come along when when you’ve settled. Or in other words, you didn’t listen to your heart, like I didn’t trust my heart or my intuition when I was younger.

I listened to everybody else around me. I was more concerned with their opinion than my own and how things look to the outside world instead of how it felt on the inside to me. That led to me getting married when deep down I really didn’t want to. I got engaged and I thought, “Oh, well in a year or two we’ll get married.” Then as soon as I put engagement ring on her finger, her mother just dropped the hammer and the wedding happened six months later. I was like, “Holy shit.” I was along for the ride. At that point. I did take her parents out to dinner, ask him for permission, but man, it’s just like they took over. Six months later, I was married and my head was spinning.

I tried forgetting about it, tried pushing it down and denying it. Coach, as you know, that just made it grow into something bigger and more undeniable.

Well, what you resist will persist, and what you look at tends to disappear. I had the same issue. Deep down, it didn’t feel right. Deep down, I wanted to date around and explore other women and other relationships, but I had to be reasonable because that’s what everybody told me I needed to do. I just had cold feet. “Once you’re married and living together, you’ll live happily ever after and it’ll just be peachy,” but those feelings never went away. Then a year later, I ran into a girl that stirred something inside me that I hadn’t felt in many years and I thought, “I gotta know what it’s like to be with somebody like that. I cannot continue to do what I’m doing. It doesn’t feel authentic. It doesn’t feel right.” So I made the painful decision to leave. The worst thing I ever had to deal with, at least at that time.

I also experienced that I was beginning to throw a lot of the other things I cared about and loved into this hole of denial and repression.

Yeah, you settle in one area of your life that makes it easy to settle in other areas of your life, and that’s what happens to the average person. They just slowly give up on their dreams and their goals and the things they really want. “Well, I got to be reasonable.”

15 years later, and I can see clearly how denying my own authentic truth around my feelings for these two gals lead me to abandon large parts of me that I cared about. It’s like it all got thrown into the hole with my feelings for the sister. Wasn’t aware of it at the time, but now I can see it clearly.

Again, when you start settling in any area of your life, then that sets the standard. Then you make excuses and you settle at other things. Whether it’s climbing the corporate ladder, starting a business, things you want to do, things you want to experience, where you want to live, maybe changing jobs or chasing that career you always wanted. Then you go, “No, I got to be reasonable. That’s crazy. I don’t know anybody. I don’t have the education. I don’t have the money, I don’t have the time. I got to get my tennis elbow fixed,” whatever the hell it happens to be. You create a story that justifies mediocrity, that justifies doing nothing.

As Aristotle said, “People do more to avoid pain than they will do to gain pleasure.” That’s why most people typically don’t reach their full potential. They’re too afraid of the pain or the potential pain involved. So they shrink from it and they do what sounds reasonable.

Anyways, to fast forward a bit, the roommate and I eventually got engaged. That was like the beginning of the end. I remember after we got engaged, lounging in bed together, she was like, “We’re gonna spend the rest of our lives together.” And I was like, “Wait, hold on. That’s not what I wanted.” I proposed to her almost as a statement of love, “I really love you.”

Yeah, I remember buying an engagement ring and just going, “What am I doing? It’s like $3,000.” It’s like 30 years ago. “That’s a lot of money. I need to take this back. This is nuts.” I just laid there in bed for hours. “I take it back. I’m gonna keep it. I’m gonna go through with it. I’m gonna hold on to it for a while.” I talked to all the girls that I worked with. All the women that were married, “Oh Corey, she’s a great girl. You just got cold feet. That’ll pass. Don’t be silly. Don’t ruin a good thing.”

But it was almost performative, like to prove to her, and myself, that I was making the right choice all those years (about five) we were together, when in reality it was her sister I truly loved the whole time.

Well, I’d say you just had genuine, sincere desire and attraction for the sister, but because of the story that you told yourself and you created around your relationship with your roommate, you were not open to exploring anything else. You denied yourself the opportunity because you got to be reasonable. “You just got cold feet, dude. The grass is not always greener on the other side.”

Once I thought about it, I realized I didn’t want to be with this girl forever, 10, 20, 30 years. And so over the next year, we gradually started having the important conversations that we’d been putting off, looking at the relationship. Eventually we decided to call off the wedding, and shortly thereafter, we broke up for good. I came home one day and she was moving out on the sly. 

It was a really hard breakup, because I did love her, but more like a close family member.

Yeah, I remember having a conversation with my ex-wife. I was like, “It kind of feels like we’re brother and sister. It doesn’t feel like a deep, true, passionate love story,” and she already knew what I was going to say because I had shared it with my supposed best friend, and he was telling her everything. I was telling him that I thought he was keeping between us because he was supposed to be my best friend, because he was trying to ingratiate himself to my ex-wife to be, so he could get in her pants. Good dude, huh?

My dad had died around the time we got together, and she was like a life-preserver for me, something solid I could hold onto as my world was falling apart. My dad was my best friend, and losing him was really hard. She had a similar sense of humor, and it was like that part of me and him that I loved could live on in my relationship with this woman.

About four years later, out of the blue, the sister got in touch with me. I was elated. Here was my chance to finally spill my guts and let her know how I felt! I said to myself that at the very least, I can finally get this off my chest and let her know that I’ve been in love with her this whole time. Very antithetical to your teachings, I know. This was before discovering your work. 

Well, if a woman reaches out like that, you’d be like, “Oh, it’s so great to hear from you. We should get together for dinner.” Invite her over. You can invite her over to make dinner or you can go out to dinner. I mean, in this case, you knew her well because you dated her sister.

So I was able to tell her, and, no surprise, she told me she felt the same way, had felt the same way the whole time. 

See? If he’d only casually dated his sister and then moved on, he could have started dating the other one. It probably wouldn’t have been as big a deal, but then again, rejection breeds obsession. Women tend to be very competitive. I can only imagine what it’s like between two sisters.

We started dating, as if out of a dream, and everything was golden for about one month. The roommate, my ex, even gave her blessing, stating she was surprised we hadn’t already gotten together, that we were perfect for each other. It seemed things were finally aligning. In truth, I was on cloud nine.

And he probably got dopey because of it.

Then, it all changed. My ex-fiancée, the roommate, started to get jealous. She had dreams where the entire family was basically putting her down and making her feel like shit, like she wasn’t chosen, and the sister was. My ex had confidence issues and seemed to project that onto “the sister” their entire lives growing up, so me “choosing” the sister over my ex (the roommate) really cut into her self-confidence and reawakened some old unhealed wounds.

She probably didn’t like seeing her sister happy, especially with her ex-fiancé. First, it was no big deal, but then she saw how things were going and she wasn’t having it. Most people want you to be happy and successful as long as you’re not happier and more successful than they are.

The result was that my ex and “the sister” started arguing and fighting more, and these girls (who are part of a really tight knit group of sisters) essentially decided that they weren’t going to let me tear them and their sisterhood apart, and so my dream girl (the sister) kinda pulled back and stopped responding to me, making it clear she couldn’t see me anymore.

Well, when that happens, you don’t chase. You just say, “Well, I’m sorry you feel that way. I think it sucks. I mean, at the end of the day, your sister initially gave us her blessing, and now she’s trying to tear us apart, which I think it sucks, but you got to do what’s right for you. You got my number. I hope you changed your mind. It’d be wonderful to hear from you, but if not, it’s been wonderful. Even the last 30 days. It was worth the wait. So I hope you reconsider. Reach out if you change your mind.” That’s all you can do at that point.

At this point, sensing the bitter end, I sent a sappy email where I ended things more officially, attempting to save face and take the high road, at the same time leaving the door open. She didn’t respond, and I haven’t heard from her since.

Well, you never try to keep somebody who doesn’t want to keep you. So the best thing to do is no-contact and let her experience what life is really like without you. She got to experience a month with you. Hopefully you didn’t talk her out of liking you in that time, but I suspect maybe you got a little dopey. Again, if she was really in love with you, I mean, it was only about a month. It usually takes six to seven weeks, and that’s if you’re applying what’s in the book properly.

So I don’t know when you came across my work if it was during, before this, or after this, but at the end of the day, she dipped and ignored you. It seems like the fact that you were getting ignored tells me that you were trying to contact her on multiple occasions and she was ignoring you. So you sent that email thinking, “Well, maybe she’ll read the email and chase after me,” and of course, you never heard anything because again, that’s what we see in the movies. Just spill your guts on a note and that’ll hopefully make all the difference. Usually what happens is nothing. You usually don’t hear anything. I sent enough of those letters when I was younger and never heard back. I was like, “Well, that sucks,” but that’s life.

So again, I suspect he was displaying some unattractive behavior when he was with her because he was over the moon and probably got a little dopey and started displaying some weakness. So the fantasy that the sister had about him and what kind of guy he was probably dissipated in the time that they were together.

I blocked her on social media so I wouldn’t be tempted to spy on her. Lately though, I’ve been poking around, thinking about contacting her again.

I wouldn’t do nothing. She’s got your number. You told her to reach out. This is the illusion of action. More of trying to pursue. That’s probably what happened, is she started backing off, you probably started to call and text more because you went into panic mode and you started fearing losing her. Unfortunately, what you fear, you attract. So what you feared that happened was getting ghosted and losing her actually ended up happening.

So Coach, my question is, is this situation salvageable? Is it EVER possible to date “the sister” of a girl one has been involved with, almost married (or even married?). 

It is possible, but you got to remember, it takes two to tango ,and this girl ignored you. In other words, you continued to reach out and you got ignored on multiple occasions, yet that didn’t stop you from reaching out. So again, the illusion of action is trying to convince you that more reaching out will fix this, when in reality you probably over-invested, over-communicated your feelings and your interest and took away the challenge. So she dipped.

So again, there’s nothing you can do. You’ve let her know that you were interested, but if she stays away, then that means her interest isn’t high enough. Her emotions aren’t strong enough to override the bad friction she’s getting from her sister.

I still see on social media that “the sister” isn’t married and doesn’t have any kids. It feels like we are really soul mates and should be together, I just fucked up so royally. I wonder if there’s any way back from this. Lately I’ve been thinking more about her and wonder if I should reach out, invite her out. I just seems like such a quagmire…

Remember dude, this girl stopped responding to you. So why is it you think more texting and calling is going to get through when she’s ignored you and maybe even blocked you from reaching out? You got to have some self respect. Nothing is possible unless this girl makes an effort. What you’re ignoring is this girl is making zero effort.

…And if my ex (the roommate) is still jealous, it’s a non-starter, wouldn’t you say?

Yeah again, because no amount of you vomiting your feelings or pleading with the girl you really want to be with is going to change her mind or her attitude when she’s ignoring you. So more getting ignored, more texting, more calling, it doesn’t help.

I kind of know it’s hopeless and I should just move on, stop being hung-up on an unattainable prize. Wanted to hear your thoughts and share my story, because I feel like it would generate some good points from you that could help the other guys who follow you.

Thanks again for all you do, Coach. 

Sincerely,

Bob

Well again, at this point, you’ve done everything you can do and now it’s up to the sister. So give her the gift of missing you. If that turns into a permanent thing, then, then so be it. It wasn’t going to work anyways. Like I said, the most important thing in the meantime, you should be reading the book, learning it, and applying it with other women.

I know that’s the last thing you feel like, but I just did a success story yesterday, as a matter of fact, on guys that did exactly that. They trusted the process, they learned the book, they learned 7 Principles To Get An Ex Back, and they stuck to it, and the girls both ended up coming back. One of them in particular had been doing so well with other ladies because he really bought into what I was telling him to do, that he didn’t even want the ex back anymore, but he was like, “You know what? We’ll see what happens.”

So again, you’ve done all you can do at this point. The rest is up to her. If she reaches out, say, “Hey, it’s awesome to hear from you! I’d love to see you.” Invite her over to make dinner at your place in the evening, following exactly what’s in 7 Principles To Get An Ex Back, and then you got to let her do all the reaching out, and then you simply make dates. She’s got to come to your house three dates in a row. As long as you hang out, have fun, and hook up all three dates, you can meet her out and pick her up, but you got to let her do all the reaching out. That way she comes to you at her pace and you’re not trying to force things, because it sure looks like you tried to force things in the short time that you were together, because she said she felt the same way. Then all of a sudden, whatever happened between her and her sister, it was easy enough for her to walk away from you. I suspect that you kind of turned her off, probably vomiting and over-communicating your interest, and you made it too easy for her.

Again, the book says to take measured steps, and you didn’t do that. You watch too many Disney movies. I know you wanted to get it off your chest, but here you are. Less really is more when it comes to the ladies. It’s a scientific fact that women are more attracted to men whose feelings are unclear, and you made yours way too clear. You just did too much, dude. So doing more of what got you ghosted is not gonna unghost you. You just got to let her be.

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 on any page, and book a coaching session with yours truly. Until next time, I will talk to you soon.

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