Dear Prudence

I’m Falling for This Guy I Met on Reddit

I’ve never heard his voice or seen a picture of him, but we have mind-blowing virtual sex.

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Dear Prudence,

I signed up for this political chat line on Reddit. There are thousands of people all talking at the same time, so you have to get in to fit in. This one guy sent me a request so we could chat off-side. I don’t know exactly what it is about him, but he turned me on big time. I’ve never heard his voice or seen a picture of him, but I’m attracted to him. No one there uses their real names, but he asked me if I was married or seeing anyone. He lives in California, and he’s 42.

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We have been flirting and for the last two weeks I have had the most amazing, mind-blowing virtual sex with him. I don’t even know what to call it, but every single thing I like done to me he already knew. Our sessions have lasted for two hours or more. Am I crazy? I’m 49, and I live in the Midwest, but I am definitely intrigued by this guy. He said the same thing about me. All I know is that he is white and I am African American. I keep myself very guarded, and I am a private person. I have basically closed myself off even more with the pandemic going on. Do you have any advice for someone like me, single and on the cusp of 50?

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—Hot for a Stranger

There’s nothing wrong with being guarded, especially if you know yourself to be a private person. Right now, you’re having an amazing time talking to someone you haven’t met but love flirting with. That’s good, too! You’re not wiring him money or buying a plane ticket, so it seems like what’s troubling you is simply the intensity of your feelings. That makes sense, too: It’s a lot harder to feel guarded when you’re really into someone, especially when that someone lives far away and you don’t know much about his actual day-to-day life. But you can feel something deeply and still make careful, manageable choices.

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If you’re intrigued by him, and you’ve enjoyed flirting with him, keep flirting! If you want to try talking on the phone sometime so you can hear his voice and see if there’s chemistry on that level, or video-chat so you can see him face-to-face, ask if he’s interested. If he’s hesitant or comes up with a lot of last-minute excuses to avoid it, that’s likely a signal that this relationship isn’t going to go any further than vigorous sexting. But a call would be a reasonable next step. Don’t try to take more than one step forward with this guy at a time, don’t suggest meeting up in person before you’ve talked on the phone, and don’t make promises or commitments to one another you can’t easily keep. If he starts asking you for money, loans, other financial favors, or sensitive personal information, that’s a massive red flag, and you should cut off contact immediately.

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If things continue, consider telling a friend about it. You don’t have to say “I think I met someone on Reddit, and we’re having virtual sex for hours on end” if you don’t want to go into that kind of detail. (“I met someone online I like a lot, but he lives across the country, and I’m not sure where things are going yet” will do just fine.) But it may help to keep you grounded if he’s not a thrilling secret that only you know about. Don’t let your guard down all at once, but don’t beat yourself up for having a good time, either. Good times are in short supply these days. Enjoy enjoying yourself!

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Danny M. Lavery is joined by Colby Gordon on this week’s episode of the Dear Prudence podcast.

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Dear Prudence,

My boyfriend hates his job. He has started applying to other ones, but he’s so negative about the whole process. He’s not applying to very many places and hasn’t applied to any of the places where he has actual connections, but even so he’s had a few interviews. I think that’s promising, but he’s so quick to say, “No one wants to hire me,” “I got the wrong degree,” and “I’m not qualified for anything I want to do.” It’s so counterproductive and it’s driving me nuts. I’d say he spends 5 percent of the effort actually applying to jobs and 95 percent complaining. I think I now spend more time looking at postings for him than he does. How do I help him lose this negativity and get it out of our house?

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—Job Search or Pity Party?

You can start by stopping what you’re doing. If you’re spending more time than he does looking for job postings, all you’re going to do is build up unnecessary resentment. Since he hasn’t yet figured out what he actually wants to do next or how to go about making it happen, finding open positions is really just busywork. You’re not actually helping him solve this problem, especially when you two don’t seem to agree on what the problem is. That doesn’t mean you should roll your eyes and announce “I’m done trying to help you look for a new job, since apparently all you want to do is complain, you miserable drone.” This would be more effective: “I get that you’re really frustrated by this process, and I’m happy to talk with you about getting a different degree, or figuring out how to get qualified for the things you want to do, or whether you’re interested in applying anywhere you have connections, but I need to limit how much time I spend listening to you vent.” That doesn’t mean he’s never allowed to vent or that you don’t care about his professional happiness. But it’s perfectly consistent with being a loving, supportive partner to limit how much time you want to spend hearing someone complain.

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Dear Prudence,

I have a good friend, “Catherine,” whom I’ve known for many years. In the last few years, she’s seen a lot of her friends drift away. She’s had a lot of issues with depression and her health, and losing friends has really hurt her. We have a lot of conversations where she asks me if there’s something wrong with her and why people seem to hate her. I usually just tell her that drifting apart is natural, especially in our 30s, and it doesn’t reflect anything “wrong” with her. Quarantine, needless to say, has made this a lot worse.

The thing is that I do know why, at least in one instance. One of her formerly close friends, “Maddie,” is still a friend of mine. About a year ago, Maddie confided in me that the reason she cut ties with Catherine is that she was going through her own depression, and Catherine’s constant negativity was hard for her to deal with. It’s true: Catherine is really negative. I have a lot of patience for that, but I get why other people find her difficult. What should I tell Catherine? “Stop being so negative” doesn’t strike me as good advice to someone who is dealing with depression. I’m worried that she’d just be insulted and it wouldn’t really be constructive. On the other hand, if a friend knew something like this about me, I think I might want to know. Catherine has asked me directly if I know why Maddie won’t talk to her anymore, and I’ve lied and said I didn’t. I already encourage her to get mental health support for herself (independently of these friend issues). I just don’t know how to respond in these conversations. 

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—White Lies Versus Hard Truth

You say Catherine is constantly negative, and while I don’t know how exactly that plays out in conversation, a few suspicions leap first to mind. Does she ever ask you how you’re doing, for example? Is she much of a listener? Does she let you finish a thought, or does she interrupt in order to explain why it’s actually bad, not going to work out, pointless, or not worth doing? Does she complain about the same things over and over again without a thought for whether her listeners are getting bored? If there are specific things she does that you know turn people off, you don’t simply have to “have a lot of patience” and ignore them. You can (gently, not all at once) bring them to her attention and ask her if she’s willing to try to change.

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I don’t think you should share Maddie’s confidence with Catherine, however. Since Maddie seems uninterested in trying to repair or resume their friendship, there’s little Catherine could do with that information besides feel hurt. Nor do I think you should speculate with Catherine about why other friends may or may not have stopped speaking with her. If anything, I think you should tell her (again, gently) to stop asking you about what may be going on in her other friends’ heads. You can encourage her to ask them if she’s done something to hurt or offend them, but beyond that, you just don’t have the answers.

Catch up on this week’s Prudie.

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More Advice From How to Do It

I’m a young straight woman looking to get laid. I’m an adult, I have birth control, and, frankly, I’m horny. The thing is, I’m a virgin—I’ve never even been fingered by a partner. I don’t feel like I need to find love before becoming sexually active; attraction and trust are important, but I’m not looking for my soul mate. To that end, I’ve gotten myself some dating apps and I have plenty of potential matches. I’ve messaged a few guys and have gotten fairly steamy over text. I know I want to tell any serious contender that I’m a virgin before we get near having sex, as I can’t picture myself being able to (or wanting to!) fake being more experienced. I need a way to screen guys and say that although I’m eager, willing, and have a lot of ideas, they shouldn’t expect 1) a sex goddess or 2) an instant hookup. What should I say?

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