#1305: “Please help me close up the proverbial ‘woodwork’.”

Dear Captain Awkward,

I’m a heterosexual woman in her 30s. For the past several years my dating life consisted of various sporadic friends-with-benefits situations that lasted for years. This worked very well for me at the time (I was busy with school). But now I am in a committed relationship, it is rather serious, and now I have to figure out what to do with these quasi-exes who won’t go away.

Part of this is my fault; when COVID started I was still single and, out of “the pandemic has frozen me in singledom forever!!!” fear, reached out. The inevitable conclusion was them continuing that contact in non-platonic ways: flirting over text (nothing explicit, but it’s obvious what their intent is), texting me at like 3 AM that they’re thinking of me, sending me gifts/cards/etc, outright asking to meet up. I don’t reciprocate or engage the flirting, but it still creates suspicious optics. I would never cheat on my boyfriend and the thought appalls me. Even if the thought didn’t appall me, my boyfriend outdoes all of them on every axis — conversation, thoughtfulness, attractiveness, sex, and, uh, me being in love with him. But I can certainly see how someone might come to that conclusion based on the evidence.

I’m not sure what to do about this. I feel like I have an obligation not to ghost people I’ve known for years (regardless of how easy that would be and how much I’d like to). But I also feel like I have an equally strong obligation to stop this. I’ve tried many things, running the gamut from evasive one-word answers, to milking COVID as an excuse to be distant, to posting pictures of me with my boyfriend on social media where I know they’ll see it, to dropping references to him in conversation, to point-blank mentioning I’m in a relationship now. With exactly one person, that’s worked. More often what happens is that they say “hey, thanks for being honest and letting me know!” and other right things, but their behavior continues and would still look sketchy to an outside observer. My boyfriend does know about them but hasn’t seen their texts/etc. It doesn’t help matters that he’s been cheated on before; he’s never expressed any jealous tendencies but I can imagine him being especially sensitive/hurt if he thought it had happened again.

Hello! Thank you for sending this eminently solvable problem my way, since it allows me to do some of my favorite things, which include: 

  1. Taking an awkward social situation that seems like it should be simple and digging into why it feels harder than it “should.” “Tell them all to fuck off with that!” “Tell them all to fuck off and then block them!” “Just _________, already!” When there is an obvious path but it feels too scary or out of reach, there are probably some reasons that you’re reluctant to go there, so let’s examine them. 
  2. Examining the “why” usually reveals both the emotional landscape and some notions about power: Who has (relatively) more of it, who thinks they have it, what common stories does everyone know about it, how those stories connect up across different kinds of relationships and conflicts, what entitlements and expectations follow from those assumptions, how to reclaim or rebalance it, what the limits are, where previously untapped sources of it might lie. Sometimes when we talk about manners we’re talking about how to show kindness and consideration for others, but a lot of the time we’re talking about treading carefully around power, and any time I can combine your weird sexts with my obsessions with manners and moral philosophy is a good day at work for me!
  3. Suggesting strategies to help people get what they need in their relationships in the context of rebalancing power, where possible, and with clearer understanding of the risks and limits when it is not. Which means sometimes we return to the direct and simple approach (“You get to tell them to knock it the hell off and block the ones who won’t if you want to!”), but hopefully making the stakes clearer makes direct conversation feel more possible than it did before. 
  4. Lists! I just really like lists. Thank you for understanding. 

So, here are four reasons why this situation is extra-weird right now: 

  1. You’re aware of your good luck in finding a solid relationship in these unprecedented times™ and are trying not to be a tacky asshole to people who truly did get you through some dry and lonely times. “Survivor guilt” isn’t the right term for it, but it’s something like that. People are fucking lonely, they’re acting out in ways that their better selves will cringe at someday, and you do actually care about these people a whole lot and you don’t want to make them feel bad if you can possibly help it. 
  2. There is no official rule-book for converting a friends-with-benefits situation into a we’re-just-friends situation. The unofficial one probably does have stuff like “Have I mentioned lately that I am no longer single?” (The ‘knock it off’ is silent) and “Have you noticed that when you move your knight to ‘Looking sexy 2nite, I miss those lips!,’ I counter with queen’s bishop to ‘Evasive one-word answers’? Also, check.” (The ‘knock it off’ is, tragically, still silent, we’ll get to why in a moment). 
  3. You’ve been socialized like hell to protect men’s feelings at all costs and not say “no” in ways that might make them feel bad; doing so legitimately carries some anxiety and friction because you’ve absorbed a million messages about how when men hit on women it’s always either flattering or harmless, but when women don’t like that it’s best to assume they are paranoid, mean, and unfair. 
  4. Many cis men have been socialized to ignore both indirect and direct “no” signals from women, and some of them really lean into that and feel entitled to push their luck until they get a response they decide is clear enough, at which time they make it maximally weird and awkward in order to punish and dissuade future rude cock-blocking from the likes of you. Your former suitors don’t have to be the worst of the line-steppers to be influenced by the paradigm or subject you to its pressures. When ‘Say no to boys only if you absolutely have to and make it really gentle, more of a soft-maybe-with-a-hint-of-I’d-love-to’ meets ‘Well, she didn’t say no in precisely those words, clearly she must like it,’ trouble follows.

Here are four steps to stopping most of this: 

  1. Change all “I can’t” and “I shouldn’t” and “Because I have a boyfriend now” and “Someone might get the wrong idea” language into “I don’t like it/I don’t want to,” especially in your conversations with yourself. Your boyfriend has been cheated on in the past, he might think something is amiss if he saw the messages, okay, but you’re not cheating, so the fact that YOU don’t want these messages is good enough reason to stop them. That’s where a lot of your power lies, within your own subjective desires and affections. 
  2. Puncture your old ummmfriends’ bubbles of “Wait, why would you assume I was hitting on you when all I did was consistently hit on you?” plausible deniability. Use specific language to describe what is happening and what you want to be different in the future. If your friends and former lovers are legitimately confused about whether conversations that were welcome six months ago are no longer welcome, it’s past time to un-confuse them. 
  3. Include a request for specific actions. “I have a boyfriend” implies the “…who is Not You, so can you stop whatever ‘this’ is? It’s weird!” part. Since it’s not getting through, you’re going to have to actually say what you want them to do. 
  4. Work way less hard at protecting their feelings than you do at making your needs known. For starters, friends get to tell friends when jokes have stopped being funny. Friends respect it when other friends say “no thank you.” People who can’t treat you like a friend even after you’ve told them how are self-selecting out of your benefit of the doubt and your DMs, so it’s time to remind yourself that it’s not “ghosting” when you set a boundary and then stop engaging with people who ignore it. 

Here’s how to apply these steps, with actual scripts and some extra “why”: 

Say you get a flirty after-hours message of the kind you’d like to shut down. 

Instead of invoking the one-word-answer or the spectral presence of your boyfriend, try this: “Hi friend, it’s always nice to hear how you’re doing, but I’d really like you to stop with the flirty messages from now on, I’m not enjoying them.”  If you get more “Hey thanks for being honest and letting me know,” and they actually listen and stop, great. 

If you get more “Hey, thanks for being honest,” but the behavior doesn’t stop, it’s time to at least mute this person’s communications and stop responding. You told them what you needed in order to be friends, they weren’t interested in your friendship on those terms, that’s hardly “ghosting.” Some of this crowd will probably do your fading for you, which is a bummer, but I can’t fault a person who chooses to keep their distance from a crush or ex,  since it’s actually one way of both taking care of their own feelings around rejection and *respecting* your boundaries. 

The thing I want to dig into more is the chance that they’ll respond with wounded pride and minor gaslighting that makes you feel like you did something wrong, as in: “Wait, did you think I was hitting on you? Just because I sent a series of ‘just thinking about you 😉 😉 ;-)’  messages at the exact time of night when we used to constantly sext each other, after you told me you weren’t single anymore and kind of asked me not to? HOW DARE you read my present behavior in the light of past behavior!” 

This is a form of “negging,” or “typecasting,” i.e. a prompt designed to convert the conversation from one where you communicate a boundary into one where you reassure the other person that you didn’t actually mean it, feel bad about even mentioning it, and grant them an exception.

It may not be a conscious power play on the guy’s part, people say a lot of things when their feelings are hurt and egos are wounded. But it’s still a power play, one that relies on socialization, where your next line is supposed to be“No, NO, obviously I didn’t think you meant that! I’m so sorry to have misjudged your pure heart!” that lets him walk away feeling justified and leaves you uncertain about what just happened and (conveniently) more tentative about shutting down future bad behavior. After all, if he didn’t Mean It That Way, it can’t really be a problem, right?


Power loves ambiguity. It loves receiving and demanding the benefit of the doubt, because it almost always benefits whenever there is doubt, and it loves the things that are commonly understood (obeyed, accepted) without needing to be stated, e.g. Will no one rid me of this meddlesome priest?Power greatly prefers conversations about intent to conversations about outcomes and consequences, and it loves both euphemisms and the kind of “fairness” that pretends that historical facts and real-world power imbalances don’t exist, or if they exist, they probably don’t apply here, because power is always both example and exception, whichever one allows it to continue on without having to change anything about itself.

Power craves reassurance. It doesn’t only want compliance, it wants the performance of consent and reassurance that everything about itself is deserved and right and just. Power never means what it says, unless of course you agree, in which case, score! “Come on, I’m one of the good guys, really,” power whines, when challenged. “You’re taking this the wrong way!” 

These are two of power’s weaknesses. These are levers you can pull. 

Which is why one way to resist this type of manipulation is to look honestly at the power dynamics and assumptions around a conflict and deliberately set them aside for now. Whatever this relationship was supposed to be like, whatever we assumed it would be like, let’s deal with what it is like. That’s what every person who tries the #notall defense wants, right? To be treated as an absolute individual and not one of a set. Cool, you can work with that, which is why from now on you’ll meet plausibly deniable jokes and boundary-crossing pokes with complete sincerity. “Since we keep misunderstanding each other’s jokes and intentions, let’s stick to saying what we mean and meaning what we say. Things have changed, and I don’t want to flirt with you anymore, even as a joke. Can I trust you respect that?” 

A second way is to replace ambiguity and euphemism by accurately naming and describing behaviors. This comes up a ton in discussions about abuse and estrangement, where the wrongdoers pretend they don’t know why anyone is mad at them. “Why won’t you just make peace with your relative who loves you?” sounds a lot different when it’s accurately reframed as Wait, are you asking me to be okay with [specific terrible behaviors, inc. sexual assault]?” Every single “Come on, lighten up” or “You’re just too sensitive” neg coms under this one: “You’re right, I’m pretty sensitive about it, which is why I asked you to stop sending explicit messages to me late at night. If you didn’t know, now you do. If you did know and just wanted to test the limits, here they are. Flirting is only fun if everyone is having fun, and I’m not.” (Maybe it’s just me, but if accurate descriptions of your behavior make you feel embarrassed and bad, it’s probably time to stop whatever that is!)

A third way is to replace conversations about what they intended (a thing you cannot possibly know or prove for certain, so no need to spend time debating it!) with concrete instructions about what you need them to do now. They had the best of intentions? Wonderful, let that be a given, now let’s back those up with some better actions along with the reassuring carrot that everybody still gets to save face and walk away feeling like the good guy…as long as the boundary-crossing behavior stops right now.

To apply this, next time a former kissing friend sends up the “I was just thinking about you, and no, my hand definitely wasn’t inside my underpants the whole time I ‘thought’ about you, why would you even ask that? j/k You know I don’t wear underpants” midnight signal flare, wait until the cold light of day, and reply with some version of:

  • “Ha, it’s never weird or awkward to be reminded that we used to bone, definitely keep doing that forever, j/k it makes me wicked uncomfortable especially now that I am in a committed relationship, and if you really want to be my friend, you’ll stop now please.” 
  • “Well, if you ever happen to ‘think of me’ during normal business hours, and it’s in the context of [an article related to my field of study][a pop culture fan thing we share][literally any non-sexual or suggestive topic of any kind], do let me know, but I’m not a fan of these late night single entendres. Let’s keep it G-Rated from now on!” 
  • “Have you noticed that when you [bring past sexy thing up][effusively compliment me][are overly-familiar][drop suggestive comments like _______] I always change the subject? Can we have an official, permanent subject change? You’re an important friend to me and we have so much other stuff in common, surely we don’t have to revisit olden times to find something to talk about.” 
  • “Say, Old Bean,* I’ve tried gently hinting that I’m done with the flirty stuff, but maybe it’s not getting through. I’m sure you don’t mean anything by it, but it’s really time to stop. Thank you.”
  • *Old Bean! My friend just did a delightful audio read-through of the first Tommy & Tuppence book (The Secret Adversary, by Agatha Christie), and I wish Americans had more words for “this is a friendly chat right now, not a flirting chat, just a friendly one, thanks a million, Old Bean, you’re a brick.” The closest ones I can think of are “Buddy” and “Champ,” like, “Look, Champ, we had a good run, but I’ll cherish the fond memories of our glory days much more if you’ll stop dragging their carcasses onto the carpet of our present friendship and posing them like He-Men.”

Now, imagine you go for more directness and get the “Whoa, hold up! I was just joking/I wasn’t hitting on you/I realize you’re ‘taken’ now, thanks for rubbing it in/It was all in good fun/Don’t flatter yourself!” defensive response, with a side of more boundary-testing.

Future You: “Phew, that’s a relief! Thanks for clearing everything up and keeping it G-rated from now on.” 

Take them at their word, be sincere and specific about what you want from now on. Removing plausible deniability and giving them a constructive way forward means they have to make a concerted, deliberate effort to continue annoying you, which is the same thing as self-identifying as a person you do not have to coddle or tolerate in your precious free time anymore.

Thanking people in advance for things you hope and expect they’ll do is a a favorite strategy of Blog-Friend Ask A Manager. It means granting people an unearned grace, but it’s often quite effective when the other person in a conflict wants to look good and feel good slightly more than they wanted to actually do good. I think of it almost as benevolent gas-lighting. “Let’s both pretend you always intended to clear this extremely low bar for good behavior! If we give you lots of praise and credit for not being an asshole, perhaps ‘not being a asshole’ will become the path of least resistance.” 

When you follow that up with a reminder of the action you expect they’ll take, it’s like a seal on the deal. “Let’s both pretend that you never meant to be a jerk in the first place, and as long as you do _______________/stop doing ______________, we can drop this awkward topic like a hot rock and live in the bubble where you are a cool person indefinitely. It’s so nice in the bubble! Join me!” 

Let’s not be mistaken, this too is about power. It can be a way of being magnanimous in victory when you know that you’ll get what you want in the end, it’s just a lot easier for people to be nice when they feel good. But there is a large reckoning and some very careful consideration due around the question of who gets to be told that they’re fucking it up with maximum gentleness and consideration for how they’ll feel about it during and afterward, because the better they feel, the safer the person delivering the necessary corrections will be. Learning to hear “You messed up, here’s how, please don’t” without covering the person who told you in an angry shame volcano is at least as important as learning how to say it.

Let me leave you with some alternate reply scripts for your bevy of forlorn former beaux:

  • “Oh, I was pretty sure you were joking, but it was really starting to bother me. Now that that’s cleared up, what’s new with that [giant subject change?]”
  • “I usually hate being wrong, but this time I’m so glad to know I was misreading your intentions. So we’re agreed, no more late-night musings on ancient history or ‘joking’ sexts, that’s all I wanted to know. Perfect.” 
  • “Look, the friends-with-benefits to just-friends transition has no official rule book, it’s weird when topics that were welcome before suddenly becomes off-limits, and I know you weren’t trying to make it weirder. But things have really changed for me, and I need us to find a new conversational lane. Can I count on you?” 
  • For repeat offenders whom you’d nonetheless like to give one last chance: “What will it take for you to stop doing a thing I’ve already told you makes me uncomfortable? Stop. No, don’t explain or apologize again. Just stop!” You don’t owe them endless chances or attention, and anybody who keeps pressing you has more than earned the block button. 

To review:

  1. There is a pretty straightforward solution to making this stop. 
  2. There were probably reasons why the obvious thing felt weird and why hints and indirect messages weren’t getting through. 
  3. There are lots and lots of ways to tell entitled former make-out partners that they don’t have to go home but they can’t stay here. I hope your true friends in the bunch will be revealed quickly and painlessly and the rest will fuck off gently into that good night.
  4. Wait, not the DEATH-good-night, just the one that means restoring a passing “Good sailing, Old Bean!” kind of vibe between you. 
  5. #LISTS! ❤






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