"I Caught Her Messaging Another Man… So I Ended It. Was I Wrong?"
2 Jun 2025 · 11 min
John ended his long-distance relationship after finding late-night messages between his girlfriend and a pharmacy technician, despite a boundary against new opposite-sex followers. The host says John's monitoring behavior and need for control may stem from past hurt, and suggests he needs to work on trust issues.
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All right, folks, we have a new Dear DSO entry on the website, and you can submit your own story or question at deardso.com. That is dear dso.com, fill out the form. And if your story or your question is a good one, I will create a video out of it for the whole world to see, or for my listeners on the Dad Starting Over podcast to listen to. The Dad Starting Over podcast available on Spotify, Apple Podcasts, or wherever you may listen to your podcasts. And by the way, if you're watching this on YouTube, if you could do me a big favor down below, click on subscribe, click on like, leave a comment. It would help me out a great deal. Thank you so very much. Now on to today's submission, which comes from, we'll call him John. Technically, this did not come via the form on the website. This came via Facebook. People send me submissions all the time and questions all the time via Facebook, Twitter, TikTok, any of those social media platforms, Instagram. Search for Dad Starting Over and you can send me a direct message that way. He says, hey there, sir. Well, hey there, John. I know you must get a lot of messages. Yes, I do. So I'll get right to it. Me and my parentheses now ex-girlfriend were long distance. She needed, she needed back surgery and was on a lot of pain meds post-op. Sorry to hear that. Right or wrong, I basically have the males on her Instagram friends list memorized. So that I know when there is a new follower. Oh, John, you're a little insecure there, buddy. Um, in our 6 months together, this is the only one I have noticed as a male, and she always told me when one DM'd or requested her, parentheses, at my request. A little controlling there. But not this guy, he says. Also, she followed him back. Okay, so there's one guy she didn't tell you about him. She followed him back. He says, I did some digging. Turns out that he's the pharmacy tech where she goes once a week, sometimes a few times a week, for her medicine slash groceries. I confront her on the new friend, which she knows I have a boundary on, uh, no new opposite sex followers on social media. Parentheses, I just ignored a Facebook request from an old female coworker out of the same respect that I ask for. She said that she was, quote, just being nice and that he messaged her. She sent the screenshot of the messages sent at 10:00 PM and 1:00 AM on separate days that were seemingly, quote, innocent, checking on her condition and again on her and, and again on if her kids got their medicine. So she has kids. Sounds like from a previous relationship. She hearted the first message and said thank you to the next. It was Thursday and that first text was Sunday. My stomach turned over. I had a sinking feeling and I broke up with her on the spot. Now I'm questioning if it was something worth breaking up over. I'd appreciate your thoughts as I'm still struggling. I've never been the one to call it off, as I think it hurts less to get hurt than to hurt someone like that. She said she was going to tell me, but she was afraid to because I would, quote, think it was so much more than it was. Then why, knowing how I would probably— then why respond knowing how I would probably feel? So why respond to that guy if you know I'm going to be pissed about it, is what he's saying. Again, nothing nefarious confirmed, but But the fact that she allowed a crack in the door that she denies was enough for me to eject. Okay, well, interesting one and one that I get and probably a lot of guys that have been hurt by women in the past get. And it sounds like you maybe have been hurt in the past. You say you've never been one to do the old breakup before, so this is your first being the break-upper, the person who dumps the other person. And over your experience with women in the past, you have developed a series of what you call boundaries, which are basically things that you will and will not put up with that happen to you. And you see this as something happening to you, that this person is potentially going to commit some infidelity, or I don't know where you're going with this, or just being secretive or whatever, but you know, like, so you told her up front, here's the deal. If you want to be my girlfriend, you have to tell me every time somebody, some person of the opposite sex sends you a friend request. Right away I'm like, if I'm her, I'll be like, ah, this sounds like you got some issues, dude, that you need to work on before you can get yourself a girlfriend. I don't think so. But she's like, okay, you got it, no problem. And you check up on her repeatedly, looking at, memorizing her friend list. I mean, all this is like, dude, now I and other dudes listening to this who have been down the road of being hurt by women will say, and we get it, but there also has to be a part of you that says I can't monitor another human being and control their behavior 24/7. That's not healthy. It's not good. And if I don't trust them to the point of monitoring them that closely, that points to either, hmm, there's something about them that turns me into this kind of controlling person, or I'm at baseline now, thanks to my past and everything else, a very controlling, insecure individual. And I need to work on that. Regardless of whichever direction, you know, your thought processes take you, I think the end result is the same. Yeah, you probably shouldn't be with this gal. Your fault, her fault, whatever. Just, and this ain't gonna work. And so you ended it. Like I say, all different kinds of ways of looking at this. John's pretty insecure. John needs some to work on himself before getting into a relationship. It's probably best for her that she's not in a relationship with John, or John dodged a bullet. And John has learned from his past transgressions, you know, or his past experience with some of these other gals, that this is the kind of behavior that leads to not so good behavior that could hurt you in the long run, whatever it may be. There's no right or wrong here except to say, uh, this is your boundary. She violated it. You have, I would assume, really thought and, and really pondered this boundary, if you want to call it that. And you've determined that this is really important to you, to the point of actually destroying a relationship over it— destroying, ending a relationship over it.
Cool.
But you know, you can't have your cake and eat it too. I find myself saying that a lot to guys. You can't do something like end a relationship, which I— going back to your message— assumes kind of long-term relationship and not feel heartache over it. Not feel bad, not feel yucky, anxious over the fact that you just broke up with somebody. It's gonna feel bad. So you either have the boundary, you stick to it, and you deal with the subsequent feel-bad emotions as a result of you breaking up, or you don't break up. You can't, you can't break up with somebody and then not feel a little yucky about it. I don't care how it ends. I don't care if they're physically abusive to you or whatever it is. A relationship ending always has those feelings of Ugh, this sucks. I don't feel like I did yesterday when we were together in a relationship. I feel kind of gross. I feel like there's a part of me missing them. And then you feel like guilt. Why do I miss them if they were the one that did bad things to me? And all this other— welcome to real life, dude. Relationships kind of suck in that way. It's the old yin and yang of life. You have the love and the romance and the partnership and everything else, but you always run the risk of it ending and you always run the risk of heartache. Such is life. This goes for every aspect of life. There's always a yin and yang and up and down to this. And what I hear from a lot of people, men and women alike, is, "I don't like that. I want to be able to do, fill in the blank, behavior, and I want there to be no negative repercussion as a result of this." So let's say, for example, that your gal was in fact on the path to forming an inappropriate relationship with this guy, the pharmacy tech. Don't know, doubt it, but whatever. Let's say that that was— if we were looking, got in a time machine, we would say, aha, she was up to no good. So let's say you made the right decision. As I often say to guys, just because you made the right decision doesn't mean that it's going to be free of the consequences of negative feelings, negative repercussions, bad things happen to you down the line in life. It's still the, quote, right thing to do. And you had to do it. And hopefully in the long run you'll look back and go, oh yeah, I can see how that was beneficial to me, how doing the, uh, making that decision was the right thing overall. It caused some, some immediate pain, some heartache, some negative feelings initially, but in the long run, best thing to do. I think that's probably what you'll see coming out of this, but it also may be a big lesson for you to kind of look at yourself, John, and say, yeah, maybe I got some stuff I need to work on. Maybe I need to work on trust. Maybe I need to work on bringing more secure individuals, healthy, mentally healthy individuals in my life so that I don't have to be constantly questioning whatever it is they're doing. And then maybe that will, in a roundabout way, help me become a more secure individual. I don't know, but you got some work you need to do on yourself. May I make a suggestion, as I do in almost all these videos? Check out our group, the Brotherhood. Help4men.com. You go to help4men.com/join or jump to Brotherhood in the menu, and you can join a group of guys from all over the world, hundreds and hundreds of men from all over the world. We get together in discussion forums, live meetings, we get together in person. We have over 1,000+ hours of content available for our members, my books, all kinds of cool stuff. So check it out, the Brotherhood at help4men.com. All right, John, thank you for writing in. I appreciate it, and thank you guys for watching, and we'll catch you on the next one.
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