Dear Prudence

Help! My Boyfriend’s WhatsApp Messages Have Me Deeply Disturbed.

Each week in Dear Prudence Uncensored, Prudie discusses a tricky letter with fellow Slate writer (and her husband!) Joel Anderson, only for Slate Plus members. This week, they dig into “Wrong to Have Snooped.”

Dear Prudence,

I went snooping in my boyfriend’s WhatsApp archived chats and came across his messages with his ex-girlfriend who he had dumped in 2020. He had always said she was crazy, and after trying to baby-trap him, he had to leave. These messages show he drove to her place in 2021 at Christmas and tried to give her a present and beg her back. I know it’s wrong to snoop, and I’ve never told him I read these messages. But any time he mentions how he would never get back with an ex (particularly that one), I feel really unsettled. I don’t know what to do— should I say something?

—Wrong to Have Snooped

Read Prudie’s original response to this letter.

Jenée Desmond-Harris: Doesn’t matter really, but how did she try (and fail) to baby-trap him? Like, what is the evidence?

Joel Anderson: The only thing that comes to mind is pretty graphic. So I’ll skip a description here and share it offline with the “How To Do It” columnists to see if it’s plausible. But in the meantime, don’t you think something was compelling her to check his messages anyway?

Jenée: Yep. I mean, of course some people are just going to be jealous and suspicious for no reason, or jealous and suspicious for reasons that go back to childhood, or jealous and suspicious in every relationship. But I tend to think that if you’re moved to snoop, something is already wrong. Either you have a reason to believe your partner is hiding something or you just sense they don’t feel the way you’d hope they feel about you.

Joel: Right. So it seems like those suspicions were grounded in some legitimate fears about his commitment to you and your relationship. There’s no need in beating yourself up over that: The damage is done, and now you learned the really hurtful truth of the matter. He was ready to run off with his ex—even after she almost baby-trapped him!

You have no choice but to confront him over this, if only because you want to beat him to the punch before he comes to you and tells you he’s moving back in with his old girlfriend.

Jenée: Wait, I actually went a different direction with my actual response. I think he just smoothed out the story about his new ex and eliminated the part where he was the loser and behaved desperately. Which is not totally honest but not a horrible thing to do. And remember, she looked through all those messages and there was no other evidence of misbehavior! Nothing even questionable! I feel like he may actually be all in on their relationship.

Joel: You know what? I realize I don’t know when LW’s relationship with this boyfriend actually started. Were they together in 2021 or not? Because you’re right: If they weren’t together, then no harm no foul. He just doesn’t wanna come off as the one who was pining for an ex, which is understandable. But if they were together, then it’s obviously a problem.

Jenée: I feel like they weren’t together when the messages were sent because her big issue is that he lied about how the relationship ended, not “he was pursuing another relationship while we were together.”

Joel: Ok, fair enough. Then, yeah. We agree. It’s not ideal that her boyfriend isn’t being totally honest about his relationship with his ex and his feelings for them—old ones or not. But let’s be real: None of us is completely and totally honest about how all of our old relationships went down and how they ended. There’s no need!

Jenée: Oh really … Let me get a peek at your WhatsApp archives then! Or Blackplanet … or your pager messages. Whatever fits the timeline and age.

Joel: Um, no. Because the other part of this column that needs to be addressed is this: Seriously, don’t go snooping and reviewing old messages. Even looking at them together, for a real attempt at radical transparency and honesty in the relationship, wouldn’t reveal much that you’d be excited to read. Let’s say you peeped out … my old G-chat logs from 15 years ago … Do you really want that in your life? I know I don’t!

Jenée: Fair. But you know what the guy in this letter is doing that’s making it hard to leave the past in the past? Mentioning more than once that he would never get back together with his ex. Like how does that even come up? Why is it even a topic on the table? There’s a lot missing here. Either he’s obsessed with her still and LW senses that. Or LW is so jealous that she’s always bringing her up and going “So what if I died … would you get back together with her then??”

Joel: That’s it! He’s still, low-key, burning a little candle for her. It’s such an odd conversation topic to still be coming up at this point in the relationship. And it seems like that’s what’s actually triggering the LW here, and sent her diving into his private messages.
Is it possible for her to be, like, “Can we not talk about this anymore? It’s a little strange.”

Jenée: Or even just do some real soul searching about whether this relationship feels like a fit and if she feels like her boyfriend is all in. My guess is no. And that she doesn’t need to do any more digital investigation to confirm that.

Joel: Yeah, the vibes are off. Maybe the way to think of it now: It’s a good data point to have. And now she can think about why she was looking through his WhatsApp archived chats and if that’s what she wants out of a long-term, committed relationship with this dude. I tend to doubt it.

Jenée: It’s one of those situations where what she found wasn’t horrendous, but all the facts and feelings around it suggest a problem. LW, I’m not saying you have to break up right away, but give it some thought. And definitely don’t “baby trap” him (or yourself) before you’re feeling more confident about things.