We’re fast approaching Valentine’s Day, one of the many holidays when my email inbox and Twitter feed fill up with ads and lists for sex toys to gift to your friends, partners, and other loved ones.

As I’ve mentioned before, I’m usually against buying other people sex toys as a general rule. The number of ways such a gift could backfire—and oh so spectacularly too—seem like a pretty decent deterrent.

There are obvious exceptions, of course, such as if you know the person really well or they’ve expressed a desire for a particular toy.

Then there are some situations where, I would argue, you should never, ever purchase a sex toy as a gift. Here are some of those.

If you’re trying to be funny
Full disclosure: I think gag gifts are stupid all around. If you’re going to spend money on a person, why not go for something meaningful instead of something that’s not good for more than a few minutes of amusement? But some people love gag gifts, both giving and receiving, so eh. If you must.

Unless you’re tempted to buy a sex toy as a gag gift, in which case I say don’t. Really, don’t. Buying someone a sex toy shows them that you’re thinking about their sex life. And if you’re not their lover or a really close friend with whom sex is an open topic, that’s going to make you come across as creepy regardless of your intentions. Like the person who gave their coworker a toy during the office’s Secret Santa gift exchange. Or like my uncle, who gifted my religious and repressed sister with a vibrator on her wedding night.

So don’t. Please, don’t.

If the relationship is new and/or you don’t know exactly what they like
Holidays, and Valentine’s especially, are most exciting to people in new relationships. It’s tempting to celebrate by getting really, really sexy. And there’s nothing wrong with that—by all means, sex it up! But you might want to think twice before you go buying your partner a sex toy in honor of the occasion.

If the relationship is new, you might not yet have a complete idea of what your partner enjoys in a sex toy. Don’t forget that sex toys are intensely personal. Some of the vibrators or dildos I swear by don’t do a thing for my friends. And who wants to drop money on an expensive holiday gift only for it to end up disappointing?

Some questions to consider: Does your partner like vibration? If so, do they like rumbly or buzzy? How powerful? What size? Do they like G- or P-spot stimulation? If so, direct or indirect? What about materials—silicone, metal, glass, something else? What kind of textures, if any, do they like? What about shapes?

If you can’t answer questions like these, then you might not know enough about your partner’s preferences. And, sure, you could choose based on what has good reviews or what other people like. But if you do, then you should accept the risk that what you choose will be a flop—and the less you know, the greater that risk.

If you can’t afford a good, safe toy
It’s an unfortunate fact of life that good, body-safe sex toys are expensive. With few exceptions, you should expect to pay more than US$50 or even US$100 for a vibrator, dildo, plug, etc.

If a toy is cheaper than that, especially a lot cheaper, then something is probably wrong with it, be it poor construction, toxic or porous materials, lack of durability, or something else. Steer clear.

If you can’t afford a hundred bucks for a sex toy right now, I feel you. I’m right there myself. But that means you can’t afford a sex toy, period. With some things, there’s nothing wrong with reaching for the cheaper option. Sadly, sex toys are not one of them.

If you’re really buying it for yourself
Let’s be totally honest here. Do you want to buy the thing because you genuinely think the gift recipient will enjoy it? Or because you’ll enjoy watching (or thinking about) them using it/having it used on them?

To be fair, in some situations, this is A-okay. If you and your sexual partner have a dynamic where they enthusiastically take direction from you (TPE, for example, or other D/s arrangements), this might be fine.

Otherwise, it’s the epitome of selfish gift-giving and could lead to the next item on my list. In general, if you have any doubts on this score, you should probably refrain.

If you suspect it will make them uncomfortable or feel pressured
This goes hand in hand with…pretty much all of the above, actually. Thanks in part to television, movies, and the like, people sometimes treat gift-giving holidays as an opportunity to deepen, reaffirm, “spice up,” or otherwise alter the state of an existing relationship.

And that’s fine—as long as you’re taking the other person’s desires, boundaries, and previously given consent into consideration.

In other words, if a person hasn’t, for example, explicitly said they’re interested in pegging, then you shouldn’t surprise them with a strap-on for their birthday.

If a partner has expressed reluctance about incorporating dildos into your sex life, then you shouldn’t give them a dildo in a gift bag for Valentine’s Day.

If a person hasn’t discussed sex openly and cheerfully with you, then you shouldn’t buy them any sort of sexual gift ever.

Again, if you have any doubts about how welcome a sex toy will be, you should choose another gift.

If you might hold it over their head later
This is true of any gift, so much so that I almost didn’t include it. But it warrants saying anyway, just in case.

A gift is a gift. It should be given freely, without expectation or “strings” attached.

Be honest with yourself. If you give an expensive, high-quality sex toy to this person you have in mind, are you going to expect something in return? Are you going to resent them if they don’t respond to the gift exactly as you hope they will? Are you going to demand the gift back, should your relationship with them grow distant in the future?

Yes? Maybe? Then don’t buy them a sex toy. Simple.