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Keeping Secrets When Dating Online — Good or Bad?

Repeat offender, Shelby, has a new question about things with her beau. (I don’t normally like to use the word beau unless I’m wearing a uniform from the Confederate Army. But since there is literally no way for you to prove that I’m not wearing one right now, I’ll let it stand.) Things are going great…except each of them has a secret. Scratch that — HAD a secret. And now, with cats unceremoniously dumped from their respective bags, there’s been some blowback. Shelby wants to know what to do about such secrets, and how not to, you know, go nuts about it. And since one of his secrets was that his ex had contacted him on Craigslist, she wants to know how to, you know, STOP that shizz.

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No sweat, Shelb. We are here to help. She writes:

Dear Jeff,
I’ve written before on this very guy, but here’s a new twist on the sitch… He moved from his town (changed job locations and everything) to move in with me in the small town in which I live (and grew up.) We both actually grew up here… Fastforward: He told my daughter he planned to propose to me…told our best friend the same story…became closer with my family & crazy brother
 (shows commitment in it’s self; Johnny is INSANE)…took on the role of father figure to my daughter…took a serious interest in her life, education, the works…together we’ve rented our dream house to start our life out… All sounds great!

It certainly does. I guess my work here is d–

Well, almost…

Aw, crap.

He claims that I’m his best friend and confidant. But recently, MY ex started calling me again and of course I put an end to that. But of course it had an effect on him.

Ok, this one shouldn’t be taking a long-term toll. Exes can be infuriating, but not when you’re clearly not having any of it. Which it seems is the case here.

Then, I had to explain something regarding my REAL employment (I thought it was a good idea to do since he wants to marry me) because my job involves law enforcement. Big whammy! I’m in a position that I don’t tell people unless I absolutely must; i.e., he’s moving in with me, etc. So I was truthful and he appreciated this but again, it had an effect.

Side note: the fact that you are secretly one of the feds (or whatever) is the coolest, most awesome thing I’ve ever heard. I’m sure it “had an effect” as you say, but again, it doesn’t seem like you were keeping something from him in order to keep something special to yourself. Just the way it goes when you’re part of the Mattress Tag SWAT Death Squad, I suppose. (Hey, if you’re not going to tell, I’m going to make it up.)

Now I find out that HIS ex has been calling him. They were on and off again for about 3 1/2 years. But never together for a full year; only 6 months at a time or less. Either way, she’s an ex. So…she calls him on the phone and tells him that one of his friends (old bandmate) had passed away. (Like he wouldn’t be finding this news out from anyone else he knows? She barely KNEW that man!) I said, “This is the first time I’ve heard you mention that she’s called you. Why did you not mention this before?” To which he replied, “Because I didn’t think it was important and the last time I had spoken with her was to ask her to bring my things I’d left behind so that I could move to ——-with all of my stuff. And because I didn’t want you to think there was something going on that wasn’t.” Good answer. BUT…because of the fact that I was hiding my employment situation and the fact that my ex had been bothering me makes me feel as though he may be keeping one eye open for HER because of this.

I don’t want to sound like a jealous nut, but it bothered me when I found this out when he mentioned it. I don’t want him to begin keeping things from me (his supposed best friend and confidant) because he’s disgruntled because I wasn’t able to confide in him my work situation. And I’d like this older ex woman he claims is a fruitbasket in the first place to stop calling him!! Gurrrr! Any advice? Thanks always, Shelby

Dear Shelby,

Ok, here’s the thing about secrets, in my humble opinion. Well, fairly humble. Ok, in my “obnoxiously over confident on this subject with nothing to back it up” opinion. I think secrets are fine. With a big asterisk.


That’s the real question, isn’t it? Is the stuff you two don’t tell one another to keep it a SECRET, or is it just something private. I think that if you feel that something needs to be kept secret from the other Craigslist person, it’s going to be trouble later. People feel that sort of thing. Everybody at Craigslist can sense a closed, locked door within their person, and it feels like, “Oh…I guess she doesn’t trust me then.”

Privacy is something else again, I think. Look, there are things that don’t I to be shared between people in Craigslist. Things that are not important, things that are uncensored, unrefined, unfiltered, and unhelpful. For example, let’s say your ex had called and your man didn’t know about it — would that have been bad? Probably not in the least. You certainly don’t give a crap about your ex, so why should it matter whether or not you tell about him? There’s probably no end of stuff that comes up in life that make NO difference, and so it’s not even that you’re “keeping it from him.” It’s just…why bring it up?

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In fact, there are some things — contact with an ex you don’t care about for example — that in bringing them up, you can actually appear to attach MORE weight to them than is even there. From what you’ve written about your man (here and in previous requests) it seems like that’s what happened here. This ex called him, he figured, “Why bring this up? It’s only going to upset Shelby, and it doesn’t matter to ME, so why bring it up?


In my relationship, I think of us as totally honest with each other in that sense — if something matters, we talk about it. If it doesn’t, neither of us feels the need to pick at it. We both feel confident that if there were something important to know about, we’d know about it. So we don’t go prying.

I have my journal sitting right out in the open on my desk. (And since we live in a studio, it takes up, oh, 40% of the square footage of our living space.) I don’t feel the need to hide it. Not even to file it on a shelf where it looks more “private.” I just know that Liz isn’t going to go snooping around. If she wants to know something, she’ll ask. (Boy, will she.) And she knows that if there’s something I think she SHOULD know about, I’ll tell her.

(Or, you know, if a really cool video game is coming out this fall. I tell her that as well. In case she might feel betrayed or something if I didn’t tell her about it. I’m just making sure.)


This one isn’t so easy, since it basically involves asking your man to be kind of abrupt with someone that you don’t know. As a guy who is pals with a couple of exes, I know what it means to feel a little squirrelly about the subject.

But here’s the thing, I think the most important question here is, do you trust him? Do you trust that if there were something going on, he’d tell you about it? You seem to be wondering if she’s still interested. But even if she IS, it doesn’t matter. Your Craigslist man isn’t 15 years old, he’s a big boy, and he should know how to fend off an unwanted advance. So…do you trust that he would fend it off? Sounds like yes.

If you don’t — you’re in big, big trouble that has nothing to do with the ex. And if you DO trust him? Let this one go. He’s not keeping this from you because you didn’t tell him that you’re the self defense instructor at the Men In Black facility in New York City, training Will Smith how to do judo on space aliens. Seems like he’s keeping it from you because it’s not important enough to bother.


Look, if he talked with her every week, and you found out about it six months later? Uh, yeah. That’s a bad one. But if SHE calls HIM with information? Hey, even if she’s gunning for him, doesn’t sound like she’s got much of a prayer with this Craigslist dude.

Good luck, Shelby! If you trust him, you have to trust him. If you don’t trust him even though he’s being trustworthy? That gets real old, real fast.

What’s your thinking, miladies? Shelby and man ok? Hello? Anybody have a hilarious guess as to what kind of law enforcement Shelby belongs to?

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