Agreed that workplace etiquette says gifting down is appropriate and gifting up is not because of the power dynamics. So, getting his boss a gift is weird, and for it to be a spa gift card (or anything in that price range, really) is weirder.

Any time in dating that I’ve had a Spidey sense that something was off or noticed behavior changes that made me uneasy, my gut instinct that something is amiss has never been wrong. This isn’t even that, though, because you seem to know he lies to you and hides things. Have you ever asked him why he started hiding the gifts? If not, I’d start there. If so, what did he say?

I have to say, gifting your female boss a massage for more than your actual gf (if he does know you’re all up in his business) is a very clear message in my mind.

You don’t like that he gives women weird (they are pretty weird!) gifts at work. He isn’t going to stop, despite your feelings. So it’s now your turn to decide if you want to keep playing this game or move on to something that maybe makes you feel more secure.

Unless they work in massage, this is kinda bizarre to me.

It’s weird to buy gifts for your boss and even weirder for it to be a gift card. Your boss makes more money than you do. Giving them a gift card is essentially giving them money, when they obviously already make more than you do.

If my boyfriend was giving his female boss more expensive gifts than he gives me, and then hiding it from me, yeah, I’d be suuuuuper suspicious and not at all happy.

I have a male colleague I sometimes refer to as “my work husband” as we have been through the wringer together. We get each other gifts at the holidays but it’s never anything on the scale of what I give my boyfriend and I am always completely up front with BF about what I give and receive.

Trust your gut.

The worst bit here is him getting angry with you for finding out. Its not like you were snooping, that was probably quite embarrassing and he should have been apologising. He may not be cheating but he probably wishes he was, he sounds like he may be the sort of person who always wants admiration/ gratitude/ a little flirtiness with other women to validate his ego. If it was all above board he wouldn’t be lying.Does he try to make you feel insecure in other ways? If he does, definitely time to move on. If its just the gifting then you definitely need to have a serious talk about it. Does he buy expensive intimate gifts for any of his male friends? I bet he damn well does not. And I bet he wouldn’t like it if you bought silk boxers and a course of spray tan for one of your male friends, And hid it. Then let him find out in an embarrassing way.