Be honest. Tell boyfriend exactly what you have told us. Tell him you want his advice, which you will follow.

This isn’t important enough to shred the relationship over. So if he says that he is uncomfortable with you wearing it, then follow what he says. HOW he answers is going to depend a lot on his ego, and how secure he feels in the relationship with you. (in other words, this will tell you a lot about him – if he is a controlling personality, etc.)

But the bottom line is – be honest. Lay it out. And accept the answer.

In general, I do not like it when couples have to lie to each other, but in this case, it might be the best thing to do if the subject comes up. I’m guessing that it’s unlikely that you and your boyfriend would run into the other friend while you are together right? Because the other friend doesn’t work with you anymore. So the likelihood of you wearing the tank top and being with your boyfriend and running into the other friend at the same time is pretty minimal.

So you could wear the tank top, and hope that your boyfriend doesn’t ask you about it (and try not to wear it a lot, only every now and then so it doesn’t look like you LOVE it). If he does ask you about it, then give him the little thrift store lie. The only reason I’m saying this (because I really don’t like the idea of lying to your boyfriend) is because if you tell him that the other friend gave it to you and you are happily wearing it, might make your current boyfriend think (even if there’s nothing going on) that maybe you are still in love/lust with the other guy and seeing the shirt is kind of like throwing that possibility in his face (even though that is not what you would be doing). Think about if the shoe were on the other foot and your boyfriend was constantly wearing this super cool item of clothing that an ex-girlfriend gave him. It might make you have doubts. That’s the only reason, in this particular case (not in general) that I think it would be OK for you to limit the truth.

If you don’t want to go to the trouble (conscience-wise) of lying (which is still not a good idea in my mind) then you should never wear the tank top, but keep in a special place, like a box of treasures that is private to you that your boyfriend does not have access to. I think this is what I would do, if I was in the situation.

I know that you LOVE Michael Jackson and ET, but if you respect your boyfriend, you should just keep the shirt to yourself. You can look at MJ and ET pictures online to your heart’s content, but if you wear that shirt around your boyfriend, you will have to lie (and possibly get caught, which will cause other problems, especially trust issues) or if you don’t lie, it’s likely that your boyfriend is going to have some serious doubts about your true feelings for both him and the other guy and it will be like rubbing salt into a wound. I don’t recommend it.

Well, you could say you saw this great tank top, and you really want it, and could he get it for you.

This is one of those stupid things where people get jealous stupidly, I think. What can you do? I’ve put away t-shirts because my wife didn’t like what they reminded her of. Shit happens.

Or you could wear it and take the risk and tell him you understand his feelings, but this isn’t about him. It’s about your love of the image. Either he trusts you or he doesn’t.

You could have that talk if you have to. Just be prepared. Men can be such babies sometimes.

@elbanditoroso I think if I told him, he would be upset that (let’s call him Roger) Roger got me this item so recently, and that it is so perfect for me. I do want to tell him, cause I want it off my chest. But I do know it would bother him.

@Kardamom The issue is, we frequent a lot of the same places and while the chance is slim that we would bump into him, it’s not nonexistant. Knowing my luck, it would happen. I don’t want to be caught in the lie, because that would make it even worse I know. I am leaning towards telling him, but maybe stretching the truth a little. “Yeah, Roger got me this shirt a long time ago….” hummmmmmmm…

Tell him and tell him you feel uncomfortable him not knowing. I don’t think you need to say that it is the most perfect gift anyone could have gotten you.

Another option is to decide a shirt doesn’t really matter and to throw it out.

This totally passed my tl;dr threshold, but from what I gathered by skimming…

My belief: If you’re lying, you’re cheating. We’ve all seen enough sitcoms to know that telling stupid lies doesn’t help anyone.

My solution to this: “Hey, honey, check it out! I got this in the mail today. Looks like my friend sent it to me out of the blue! Isn’t it neat-looking?”

If the response is: “Grumble grumble, I’m a jealous person”, my answer is “Eh, lighten up. It’s an effing t-shirt. If it’s that big a deal I’ll pay him back for it.” If the response is “Yep, it’s a shirt, all right” then cool, no problem. If the response is “Wow, Michael Jackson and ET?!? Is there one in my size?” then get him a link to the Zazzle store where your friend bought it.

I don’t see why there’s so much drama between couples about things that don’t matter.

I don’t really think you can maintain a friendship with this other guy in light of the past. I really don’t think you should have accepted the gift, but since you did you have to be up front and tell your boyfriend where you got it if he asks.

He may not ask.

The situation as I see it, is Black & White, you’re not a Bad person for accepting this gift, nor a Dirty Diana, you should feel no guilt. Tell him if you Wanna Be Startin Somethin & he feels like flying Off The Wall, then you say Leave Me Alone & Beat It…i’m no help am I?

“This ‘ole thing? I’ve had it for ages.” MJ has been gone for 3–4 years. ET was popular 30 years ago. Totally believable.

Why would you wear it when you are with your BF? You will be thinking of xBF#2 when you wear it. I’m guessing you have other things you can wear. Pack it away and save it for a rainy day.

BTW, You know that soft denim shirt BF#1 wears? The light blue one that you like so much? That one. Well, Ashley from the office bought it for him after they had sex in the dark, unused office down the hall from your desks. It fits him perfectly doesn’t it?

If you lie and wear the top I would put money on karma biting you on the arse by making sure you run into man number 2 while you are with man number 1 and man number 2 will mention said top.

Tell him where it came from and that you like it and want to wear it but wanted him to know about it.

@deni – someone is going to be upset. Either you or the boyfriend. The way you have described it, someone is going to feel hurt.

I’m not sure what right the BF has to feel hurt – are you sure that you aren’t projecting your own feelings? Maybe he isn’t as super-sensitive as you think.

I still say – express what you want – he may have to live with a little short term pain. But he will have a happier girlfriend as a result. Seems like a good trade to me.

I think I’m changing part of my answer. I don’t think you should lie about it. But you should also not wear it, you should just put it away in your private treasure chest.

You are right @deni that there is a small chance that you will be found out, if you lie about it, and that will hurt your boyfriend’s feelings and possibly make him not trust you, not a good way to be in a relationship.

Unless you think your boyfriend is 100% able to not feel a twinge of jealousy (because you will be thinking about the other guy when you wear it, even if you don’t plan to think about him) then don’t wear it. It would kind of be like poking him with a pin every time you do it.

Next time the other fellow offers you a gift, tell him gently that it wouldn’t be a good idea for you to accept it because you don’t want to hurt your boyfriend’s feelings by displaying whatever it is, even though you appreciate his (the other fellow) gesture.

I think that because of the previous lack of full disclosure, you have to tell him. Something like this…

“Hey honey… this is really awkward. So-and-so sent me this tank top in the mail, which is partly totally awesome because the shirt graphic is totally cool, and partly creepy because I don’t even see him or hang out with him anymore. Anyway, I do really like the shirt but I don’t know about wearing it this summer because of who it’s from. I really don’t want you to feel weird or anything because this guy sent it to me. What do you think?”

He’ll either be OK with it or not. If not, ask him if he’s more comfortable with you cutting out the image and either hanging it on the bedroom wall or sewing it onto a t-shirt that new boyfriend buys for you.

Tell new boyfriend you love him and appreciate his honesty.

@Cupcake Now that is indeed the best answer : )