Dear Fuck-Up: When Does Flirting Cross the Line?

I slide into someone's DMs every now and then, but never with the intention to cheat

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Ask A Fuck Up

Dear Fuck-Up,

I have been in a committed relationship for a little over a year now, and I am fairly confident that I will be with this person for the long haul. However, I still find myself occasionally wanting to engage in harmless (?) flirting with other people, usually in the form of DM-sliding and Snapchat-sending.

These messages are never sexually explicit — not once have I sent a nude photo or suggested (either directly or indirectly) that I want to hook up. As soon as the conversations steer towards a sexual path, I shut them down. And if given the opportunity to hook up with someone else, I am 100 percent certain that I would say no. But the awareness that I am knowingly straddling a razor-thin line between friendly and flirty makes me feel icky (for lack of a better term).

I would not mind if my partner engaged in this same behavior with others — my philosophy is that the line is not crossed unless there is an intention to hook up and/or become romantically involved. And I'm sure my worrying would be reduced if I had an honest conversation with my partner about it, but it feels strange asking for permission to slide into someone's DMs every now and then.

So, Fuck-Up, as an objective third party — at what point does flirting outside of a relationship go too far?


Attention Seeker

Dear Seeker,

I can’t really tell you how an honest conversation with your partner about this would go. Do they feel secure in your relationship? Are they a flirty and outgoing person? Have you talked in the past about what either of you thinks constitutes inappropriate behavior? I have no idea, because you haven’t provided me with a single bit of information about this person you think you’re going to be with “for the long haul.” In general, though, I would say that if you’re writing to an advice columnist rather than actually having the conversation, you aren’t really sure that doing it would lessen your worry.

And if you’re writing to me specifically, odds are you’re too old to be sending Snapchats to anyone. It’s weird and you should probably knock that off. As to the DM-sliding, I’m not sure it’s possible to be both truly flirting and sending no indirect hints that you may want to do something sexual with a person. At some base level the whole point of flirting is the hint of sex, so I’m guessing at least some of the people on the receiving end of these flirtatious messages do think it’s a possibility.

Hard to say what those people think though, because you have also provided me zero information about them. Are they receptive to your messages? Do they know you’re in a committed relationship? Are these people you have online friendships with or are you simply sending out DMs to people you barely know? In the latter case, it’s likely they find this a bit annoying. In the former, the issue here isn’t just what your partner may consider to be boundary-crossing because even if she is perfectly fine with the whole thing I still think it’s a bit difficult to justify flirting with someone who may very well be interested in you (and assumes you are interested in them, due to the flirting) then shutting it down the moment the conversation “steers to a sexual path.”

Listen, I’m a big flirt myself. It’s fun and can be done in a way that brightens the day of the person with whom you are flirting. I don’t think you’re doing this to brighten anyone’s day though, Seeker. I think you’re doing it because you imagine these people’s feelings aren’t quite as real as your own and that they exist to give you a little jolt of excitement. This may or may not constitute a breach of trust in terms of your relationship, but either way I think it’s a bit rude. A little ill-mannered and selfish. You may be the only person who meaningfully exists in the letter you wrote to me, but you are not the only one in the world.


A Fuck-Up

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