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Boss hits on me, I'm gay, but I don't want to ruin things with him
June 14, 2014 7:08 AM   Subscribe

My boss hits on me. I'm gay and he doesn't know it. But I don't want to end up souring my relationship with him because I think he could help my career. And honestly, I otherwise enjoy working for him and do think I can learn a lot from him too. It just makes me uncomfortable when he hits on me just because a) it's awkward. But also b) because sometimes I wonder if it's why he keeps me around. (Although he has been really positive about my work and I do think my work is very good, to be honest. But it still makes me wonder sometimes.)

Sorry in advance for length.

I do some sports writing for a website while I separately work full-time to earn my real salary. The sports writing pay is peanuts, but I love doing it and my hope is that one day I can get a real job writing about sports. The website I write for is run by a journalist who is very respected in his field and has a lot of experience, and a lot of connections. Many people who have written for his website have gone onto do good things for very reputable publications and have real careers in sports writing. It's a lot of extra work and stress to have a full-time career and be spending all my free time doing the website, but I generally really enjoy it and can't imagine not doing it.

The one problem that I am not sure how to navigate is that I am female and my boss who runs the website hits on me. It isn't super blatant or creepy, but it makes me uncomfortable sometimes. We've never met and we live approximately 5,000 miles apart. He only knows what I look like (kind of) because I have been in wire photos covering certain events and he's spotted me. (Sometimes I'm the only woman covering certain things and we use the wire photos for our website.) But I don't know if I should do anything about it, or just try to avoid lengthy, late-night chat sessions and try to continue getting experience with the website. I definitely do not encourage the flirting or comments. Sometimes I actually am kind of rude to him, but I think he interprets it as me being feisty or playful when I am actually serious. He doesn't say that, but it seems it could be the case. He definitely doesn't notice that I try to change subjects sometimes (perhaps not well enough).

Here's an example of what I am talking about. We're talking via gchat and he says he has a random question and asks for my shoe size. I tell him that's a weird thing to ask someone, but I don't care and give him my size. He makes a joke about my shoe size for my height, and then teases me for being short. And then he says: "I have a thing for short girls, much like you have a thing for ____ LOL" - it was a joke about a certain athlete I joked was hunky before. Another example is me asking if he can look at a draft I wrote and he says "I'm enjoying talking to you too much to look at it." (Literally the only reason I was talking to him was to try to push him to read my draft, and I was just asking him about an event he covered - small talk.) One time I sent him a media conference call recording and he said he heard me laughing and it was "cute." (I wasn't laughing -- I think he heard some other background noise. Whatever it was didn't sound cute. Haha.)

The thing is, I have a very easy out. I am gay and I have absolutely no interest in men. He doesn't know this. Part of me thinks I should say it so maybe he will back off and treat me, to be honest, like one of the guys who writes for the website. But part of me wonders if now that we've been talking for so long and he very possibly may have misinterpreted our relationship as being flirtatious, if I tell him I'm gay it may damage his ego and make him resent me. I understand my job is not to protect heterosexual men's delusional egos - believe me. But I did have a former boss who was really helpful toward me, giving me career advice and stuff, and then someone told him I was gay and he kind of stopped being helpful toward me. Maybe it was just a coincidence - I can't be sure. My relationship with him was never really flirtly -- we worked in person, so that probably makes a difference -- but I wonder if he viewed himself as being sexually attractive to me and once he realized that wasn't the case, he didn't get any ego boost or power trip from advising me anymore. My current boss and my former boss seem similar to me in that they both are at the top of their fields and can be kind of know-it-alls who see themselves a certain way. At the same time, they do really have a lot of insight and expertise to offer someone like me. Another case study, although not of a boss, is a friend of mine. We were friends for several months and worked on our college newspaper together, had the same sense of humor, etc. Just got along well. And then I told him I was gay and he was shocked and said he thought I was into him. The thing is, I was just being normal the way I would be with anyone. Clearly, joking around and generally being friends with a guy can be interpreted as romantic feelings by men since I am a woman. This was sort of news to me, because the joking and such between him and I never veered into a sexual realm at all and I didn't think anything of it.

So, back to my current boss. Writing about sports is my dream and there's a very narrow path to earning a living writing about sports - it's very competitive and difficult. Writing for this guy who hits on me sporadically may be my only/best path. This is about practicality, not principal for me - it's not about me wanting to tell someone they are sexist or homophobic or creepy or anything. It's just about making this work for me. And I don't think my boss is a bad person - probably just immature and only unintentionally sexist. I did tell one of the guys who writes for the website that I am gay. I've hinted, but never outright said my boss hits on me. The co-worker just says that our boss is immature and awkward, but not a bad guy. So. Is there a way for me to mitigate this? What should I do? Can I get him to not do that, but not feel embarrassed/ awkward/ hurt/ resentful about the fact that he has been hitting on me? Lying now and saying I have a boyfriend, for instance, would be really hard since I clearly don't, and I'm not sure that would stop "innocent" flirting anyway.

All perspectives would be great. Thanks!
posted by anonymous to Human Relations (30 answers total) 3 users marked this as a favorite
 
"I'm sorry, maybe should have told you this before but I'd always assumed we had a purely professional relationship. The thing is, I like women, and the constant flirting is making me feel uncomfortable. I would like to ask you to please stop hitting on me so we can move forward with a purely professional and mutually beneficial relationship."

Perhaps before doing this, start shopping your resume and portfolio around to other sports outlets you can write for; it's possible (probable?) that he will not react particularly positively to this news.

I am not saying women ever need to apologize for turning a man (or indeed a woman) down, I'm just saying that in an employment context where I assume there is no HR department to turn to, diplomacy is the only way out, no matter what the genders or gender preferences involved. Nor am I saying you have to out yourself, but it can provide a really bright line saying 'You shall not pass" (so stop trying, thanks.)
posted by feckless fecal fear mongering at 7:19 AM on June 14 [2 favorites]


Figure out exactly what you'd need to tangibly benefit from this job in a way that would persist independent from this guy. Reference letter? X number of publications? Introduction to a certain person? A full-time writing gig?

Figure that out and start pushing for it. Continue to deflect and avoid. Then when you have what you want, limit contact a bit and come out to him if you want to. Don't announce it, just "my girlfriend and I are going to catch a movie, any suggestions?" or similar, like he already knows, so he can save face.
posted by the young rope-rider at 7:22 AM on June 14 [37 favorites]


I don't think you need to use your sexual orientation as an excuse or a front, but you need to get a handle on this.

"Boss, I'm uncomfortable with the flirtatious tone of some of your emails. I'm really enjoying working with you, but would prefer that we keep our relationship professional."

You can't control his reaction, and it would be very unfortunate if you lost your gig as a result, but I think you realize this will not get better on its own if you don't speak up.
posted by Sweetie Darling at 7:25 AM on June 14 [12 favorites]


The next time he crosses some weird boundary in your chats (shoe size? not reading your draft?) you need to straight up say "Dude, that's not cool. I don't want to have a flirty relationship with you, I want you to treat me like exactly one of the guys who writes for the website." Do not say sorry, do not backpedal and apologise for leading him on by being a woman, etc.

And then when he crosses boundaries again, ignore those comments. Literally just skip over them and carry on.
posted by DarlingBri at 7:38 AM on June 14 [14 favorites]


Do you have to be dealing with him in chats? When writing for a website, I had a co-worker with very bad chat manners. I just only dealt with him in emails. There does come a time when you have to tell someone to stop, but I'd experiment first to see if he just acts stupid in chat.
posted by BibiRose at 7:50 AM on June 14 [7 favorites]


Ugh. I'm sorry you're dealing with this garden variety bullshit. I agree with the rope rider, identify exactly what you need to get from this guy or learn in this "job," get it and move on. Don't look back. You're not "lucky" to be working for this assclown, you're talented and driven. Use your talent and drive to move up or move on.

If it were me, I wouldn't share *any* of my personal life with him. Also, any time he says something off, take a moment to say, "well, that's weird... so back to the assignment." No friendly banter beyond "yeah, the weather's good."

I don't think telling him you're gay will defuse this situation. Sadly, he's just using his relative position of power to indulge in paternalistic mind games. How dull. Don't make it more interesting for him. I mean, don't hide something like that if it comes up but keep your focus on the prize -- the next better gig.
posted by amanda at 7:54 AM on June 14 [17 favorites]


I think the easiest way to stop this is not to engage in it and just go purely business.

Knock the the late night IM sessions on the head and steer well clear of the creepy / crazy stuff about your shoesize, just don't engage with it, and this guy will get the message.

I know where you're coming from in trying to play it to your advantage and keep him on side but playing on your flirtatiousness is often counterproductive in being taken seriously professionally or for your self esteem as a writer or as a person either!
posted by Middlemarch at 7:57 AM on June 14 [2 favorites]


Your boss is the type of person who thinks it is appropriate to flirt with female underlings and allows it get in the way of actually getting work done.

I think you can take from that a lot of important information about his maturity levels and views towards women and extrapolate from there to his likely reaction to being told he's hitting on a gay woman. Either he's going to double down with 'can I watch?' or he's going to be pissed off.

Deflect what you can, push hard to get everything you need from this opportunity and get out of this environment. You don't want to take a principled stand (and I don't blame you for that) and there's not really a half way measure that's likely to work.
posted by jacquilynne at 7:57 AM on June 14 [6 favorites]


The thing is, I have a very easy out. I am gay and I have absolutely no interest in men. He doesn't know this. Part of me thinks I should say it so maybe he will back off and treat me, to be honest, like one of the guys who writes for the website.

More likely, on finding out you are gay he will continue to be inappropriate but with new topics (asking about 3-ways, telling you he'd love to watch, or that he could be the guy to turn you, etc.). I don't really have a useful answer on how to get him to treat you like a professional, but, I think it's important to give up on the idea that outing yourself will end the flirting, so that you can make a realistic plan of action.
posted by oh yeah! at 7:58 AM on June 14 [27 favorites]


With one change, I like feckless's script: I would recommend dropping the bit about "I like women", and change that sentance to simply The thing is, the constant flirting is making me uncomfortable.

Unless you were in the sex trade, it's no-one's business what your orientation is: straight, bi, gay, undecided, whatever. And yeah, I'm afraid I have to agree that telling him you're not interested because you're gay will only worsen the situation --- he'll take it as 1)you're blowing him off because you're really saying he's not 'man enough' for you; or 2)you're a tease and a flirt who has been leading him on; or worst of all, 3)'she wouldn't be saying she's gay if she'd had a real man like me before'. None of those options are good ones, for you.

If at all possible, stop chatting with him, by text or by phone: conduct all discussions through email. The thing is, it's way easier to filter what you're saying when you have to email, rather than the no-filter instant mediums: its easier to think about things when there's at least a bit of a delay. And it's easier to skip over and ignore if he writes about things like thinking you're cute or requesting your shoe size.

And if that doesn't work: lie. Tell him your husband doesn't like the things this guy is saying to you --- you're 5000 miles away, Boss'll never know differently.
posted by easily confused at 8:06 AM on June 14 [3 favorites]


Your boss is unprofessional, regardless of your sexual preferences. Act accordingly, however that may be.
posted by oceanjesse at 8:07 AM on June 14 [2 favorites]


I worked in journalism, I think this is just the culture. Also, I was also expecting to read some pretty fucked up shit, and honestly? That's about as low level as it gets.

I'm not saying it's right. I am telling you that you should ignore his overtures and keep doing what you are doing.

If you want to keep writing, just ignore him.

If he ever says anything a notch above the shoe size comment - YES - just immediately end the phone call.

Like I said, only call him out if you want to get into a conflict with this fellow. He sounds like a dinosaur. I feel like you can navigate this and get what you want out of the deal. He's 5,000 miles away. He's being flirty, but not overtly sexual. I think this is just how he relates to women and it's not personal against you. Some men like to subtly demean women by referring to them all in a flirty objectifying way, like I said, he's a dinosaur.

It's his website. Confronting him about his communication style with you will not get you the result you want. You might be able to gently train him out of relating to you in a flirty manner by ending the call each and every time he does it, but that's about your only strategy.

I think the reality is you can't significantly change this guy. If you are worried he's flirting with you specifically - nope. I don't think so. I think it's just the way he might treat all attractive women of a certain age.

Are you really going to let this be A Thing? Ignore it and pursue your goals. This guy's attitude towards women is not your concern, don't take on that battle. It's pointless.
posted by jbenben at 8:12 AM on June 14 [18 favorites]


Echoing the above sentiments that it would still be just as inappropriate for him to be hitting on you if you were straight.

This is sexual harassment and should be treated as such. I would just politely but firmly say that his "jokes" are making you uncomfortable - and they are jokes, right? He wouldn't be trying to actually hit on one of his staff, would he?

You know - give him he out that he was just messing and got carried away, but you've also sent the message that "I know what you're really doing".
posted by EmpressCallipygos at 8:15 AM on June 14


Also, in a certain way, I'm sure he uses the website to cultivate relationships of a distant-but-flirty nature that he's possibly "testing" you out for - late nite chats that turn sexy, etc., etc.. It's like a version of a work crush, except you guys are practically internet strangers and will remain such.

If you don't want to be that for him (maybe he thinks it is likely one of the perks of his role, even if this all happening outside his conscious awareness?) continue to pleasantly change the subject or end the call.

Like I said, call him out only if you want to stop writing for the website.

The stuff you described is so mild, if you called him out directly, he wouldn't "get" it. I'm pretty sure that's just how he thinks women are treated.

Some battles are worth fighting. I think you can let this one go. Let his wife/daughter/gf/neighbor/best friend's wife set him straight about how inappropriate it is to objectify women. Leave it to someone closer to him. If you bring it up, he won't hear you, and you'll lose the writing gig.

Good luck.
posted by jbenben at 8:22 AM on June 14 [3 favorites]


This is sexual harassment and not something you want to encourage regardless of your sexual orientation.

It is a really, really bad idea to encourage your boss to hit on you inappropriately in hopes that it will someday lead to career connections.

Because A) it won't, B) don't think that situation won't escalate, and C) this is something that can really only get worse rather than better.

I'm not encouraging you to quit the job, per se, but I would shut down this behavior right away. If that means you suddenly stop getting assignments, well, did you really want to be getting published only because your editor wants to get into your pants?

Also, I would start seeing how you can leverage this writing gig into different writing gigs for other publications where this is not part of the dynamic.
posted by Sara C. at 8:26 AM on June 14 [3 favorites]


I think deflection is a good tactic here, as there's not a boss or HR who can tell him to knock it off.

I would not respond to any flirtatious comments.

I would limit the number of openings you give him, like calling a player "hunky," even though of course you shouldn't have to (and I am not in any way blaming you for his bullshit). I think he's more than proven that he can't handle a normal collegial jokey relationship, so I'd back off the jokes and friendliness on my end. You don't have to go to chillingly formal, but several degrees cooler might help.
posted by jaguar at 8:30 AM on June 14


I (deliberately) have not looked up the gender(s) of the people commenting here, but there is an interesting Thing going on with people saying "just ignore it" when compared to the current MeTa thread on sexism on MetaFilter, where 'just ignore it' seems to have consensus as something women shouldn't do, because it just enables sexist behaviour.

I'm in the 'don't ignore it, shut it the fuck down, and if you feel like it (because you have zero obligation as a woman to do so), educate him about why what he's doing is wrong' camp.

And update your resume and shop it around. This is a toxic work environment, even if you're separated by 5000 miles, and you deserve better. You deserve to be treated as a professional working person, not as an object, even in the most plausibly deniable ways.
posted by feckless fecal fear mongering at 8:37 AM on June 14 [1 favorite]


Women need to learn how to ignore and/or deflect sexism when the cost of speaking up is too great, either to our physical safety or to our financial well-being. The asker has said she doesn't want to take a principaled stand; she wants to keep her job. It sucks that she has to make that choice, but it also really sucks, a lot more, to put blame on any individual woman for enabling sexism rather than where it belongs, on the harassing boss.

OP, do what you gotta do. You don't have any great choices here.
posted by jaguar at 8:41 AM on June 14 [20 favorites]


Sometimes I actually am kind of rude to him

Stop being rude. Start being 100% professional, 100% of the time. There is no room for halfway with him.

but I don't care and give him my size

Start caring and stop answering questions like this.

I try to change subjects sometimes (perhaps not well enough).

Always change the subject if it veers into something personal. Have a stock list of questions/topics about the work to ask if something like shoe size comes up: "What do you think about a story about X?" Do not engage. Just completely ignore. If he persists, politely say "I'm not sure that's relevant. What do you think about a story about X? I think Y is an up and coming athlete with Z interesting aspect."

Writing for this guy who hits on me sporadically may be my only/best path.

Are you sure that is the case? I'm no sports fan but there's a zillion websites on a zillion topics. Start looking around for some other options. Are their female sports writers you admire? Start networking. They'll likely have been in your shoes (regardless of size - ha).

Can I get him to not do that, but not feel embarrassed/ awkward/ hurt/ resentful about the fact that he has been hitting on me?

Probably not. Your sexual orientation isn't relevant. I'm not saying hide it. I'm saying it doesn't matter in this context. Presumably you wouldn't like his behavior if you were straight. And him finding out you are gay isn't going to suddenly transform this dinosaur. Stick with "not relevant to the topic at hand, what about work topic?"

avoid lengthy, late-night chat sessions

Excellent idea. Stick to business hours, if at all possible, as another way to reinforce the professional aspect of your job. Stick to email only. If he asks inappropriate questions in emails, it's easier to ignore.

Good luck.
posted by Beti at 8:41 AM on June 14 [8 favorites]


jaguar, I apologize profusely if it seems like my comment came across as blame. I did not intend for it to be that way, and I am very sorry that it seems to have come across that way.
posted by feckless fecal fear mongering at 8:45 AM on June 14 [1 favorite]


I'll also say that, if this is an unpaid freelance writing gig, you ABSOLUTELY can find another one where this isn't part of the culture. I don't know sports writing, but I've been a freelance writer online for low or no pay, in a few different verticals, over the course of the last five years, and I've never experienced anything like this. And if you're even vaguely talented and professional, it shouldn't be difficult at all to find more outlets for your writing. "Someone is willing to publish my writing" isn't worth constant sexual harassment.

If it's a fully paid thing, that's a little bit different, and in that case I would probably concentrate more on hanging onto it until I had enough clips to move up the ladder. But even so, I think your best bet is to shut down the flirty talk in whatever way doesn't burn bridges, not to encourage it in the hopes that it will get this guy to help you in some way. Because it won't.
posted by Sara C. at 8:50 AM on June 14 [2 favorites]


Since no one else has said this; document these incidents. Hopefully you will just be moving on anyway and he's probably just a garden-variety douchewad, but just in case: keep copies of your chats and communications. Hopefully he won't escalate to sending dick pics, or showing up unexpectedly at your residence. Hopefully you won't run into him in person someday and he'll try something. But he is a risky person, so treat him as one.

And don't mention that you're gay. He's the type who is very likely to be homophobic as well as sexist. None of his business anyway.
posted by emjaybee at 9:04 AM on June 14 [1 favorite]


Nthing the young rope-rider's superb advice: eyes on the prize.

Also seconding Beti's advice: try to keep to email. Maybe you could utilize gchat's "invisible" mode now and then so that you just don't have to deal with him as often.

Sorry you're dealing with this. I empathize!
posted by nicodine at 9:26 AM on June 14


So you want to know if you can deflect your boss's heavy-handed flirtatious banter without alienating him so that you can collect any possible professional rewards that might come with playing along? Sure, but you're probably not the first young woman he's tried these tricks with, and gossip in your narrow field of journalism travels pretty fast and far. You're not going to want to be someone who got a story assignment because she was great at bjs (or virtual bjs.)

Suddenly getting all chilly and professional is just going to make him ask questions ("What's wrong?") . I'd guess that it's the banter he likes more than any actual hot action, so don't play along. Don't respond to the jokes, act like you didn't hear them or didn't understand them, and steer the conversations back to the actual work.
jbenben's right, too.
posted by Ideefixe at 9:28 AM on June 14


This man is not your boss. This is a gig, and this website is a likely a vanity project for this fellow.

This is a semi-professional situation, at best.

I think you can deal with this without making it about you and him, and I think that's the smart play here.

If this were your actual job, or you were dealing with this man in person, and/or his was in a professional relationship with you, my advice would be different.

For both of you right now this is like a paid hobby, and that's fine. In that context, his demeanor towards you isn't terribly egregious. He hasn't outright propositioned you, or even talked about your boobs or anything. He's complimented you and he's been too friendly compared to what you are comfortable with from him.

Everybody here is hung up on your misuse of the term "Boss." You are doing yourself a disservice by framing this situation into something it isn't.

Learn how to set boundaries without vilifying the other party. This is a useful and diplomatic skill that will serve you well professionally and personally as long as you live.
posted by jbenben at 9:42 AM on June 14 [2 favorites]


In addition to all the other good advice here I suggest that you make sure your gmail has the "log all chats forever" ticky box checked off for gchat. I can't remember if this is an available option from the separate gchat app itself, so if not, you should always use the chat option from the bottom left corner of your email inbox.
posted by elizardbits at 9:51 AM on June 14 [4 favorites]


Learn how to set boundaries without vilifying the other party. This is a useful and diplomatic skill that will serve you well professionally and personally as long as you live.

I agree, and I'm wondering if your "one of the guys" normal mode of being is complicating things a bit, because this guy is reading your comfort with banter as flirting, since a straight woman doing the same things you're doing might very well be flirting. Which still doesn't make it ok that your supervisor (semi-professional or not) is being skeevy.

How would you respond if a woman were being overly aggressive in flirting with you? I realize it's not going to be the exact same skillset, but maybe you can figure out what techniques from that situation would work in this one?

I could be totally off-base here, but you seem to be making an assumption that because you're not attracted to men, he shouldn't be treating you as a potential sex partner. He shouldn't be treating you as a potential sex partner because it's a professional situation, and (again) it sucks that you're having to deal with it, but your orientation is secondary here. So imagine a situation in which an actual potential sex partner were hitting on you much too much, and try to behave with him mostly the way you'd behave with that hypothetical her.
posted by jaguar at 10:15 AM on June 14 [2 favorites]


Wow, I really disagree on not logging chats. I think you most definitely should keep any and all correspondence with this guy.

I also think you should explicitly state that you want this relationship to be solely professional; he may not understand, or he might for a while and then slip back into the same behavior. But he might stop if you say this, and it is a good idea for you to be absolutely clear for your own peace of mind anyhow--it'll stop the "maybe I haven't been clear enough" run around in your own head. (For reference, in my case when I said this he listened for about a month and then seemed to forget; I am very glad I specifically stated I wanted only a professional relationship anyhow, mostly because any stupidity after I said that was clearly his fault; I was no longer worried that I hadn't been clear).

I also feel compelled to mention that most men, even in male-dominated spheres, are not this clueless. You should start looking for other mentors, of whatever gender, who will treat you with respect; they exist. So do many who can keep up a "one of the guys" kind of interaction. It is definitely worth looking for other mentorship options.

I have some mixed feelings about this, but I also tend to make sure my colleagues hear about my partner (male) and I ask about theirs; it feels appropriate to talk about family (in a light way) with work colleagues, and it has the side benefit of labelling me as not a romantic option in their minds. Are you generally out with your colleagues? There are plenty of reasons it might be right for you to be so that have nothing to do with forestalling doofuses like this, but if that happens as a side benefit, yippee? (I wouldn't come out or claim a nonexistent partner of any gender as a means of stopping this guy in particular; might not work anyhow, might be misinterpreted, etc. But as a future plan, being verbal about your orientation might be worth considering).
posted by nat at 2:09 PM on June 14 [2 favorites]


If the OP tells this guy she prefers women romantically, then she's putting her intimate life on the table for further discussion.

OP, talk about work only. Nothing personal, or even personal preferences (like saying someone is "hunky.")

Sara C is correct that you may easily be able to find other gigs, and you should do that!

Best of luck. Writing is a noble profession.
posted by jbenben at 9:48 PM on June 14 [2 favorites]


It's none of his business that you are gay, and I hate that you need an out at all. Tell him if it is important to you that he knows, by all means, but telling him will not help this situation and frankly, may escalate it.

In an ideal world, I think you should literally type, "Please stop flirting with me. It is inappropriate." But I know life is more complicated than that. So, if the conversation is concluded to your satisfaction (he answered your question or finished his review or whatever) then I would consider responding to his nonsense with, "ok let me know if you need anything else. Talk to you later, bye." Or just... don't say anything. At all. Just let the last thing he typed just sit there so he can feel as awkward as you do.

At that point, if he presses it, "hello? hello?" or if he brings it up later, then ta da! Now you CAN say, "It seemed like you were flirting with me and it made me uncomfortable. That needs to stop."
posted by juliplease at 9:25 AM on June 15 [3 favorites]


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