Hello all you frightening post-Yuletide skinsacks, and welcome to Ask Dr. NerdLove, the only dating advice column to top the list of best games of the year.
This week, we’re answering the hard questions to help you go into the new year with clean consciences and dirty minds. How do you tell your girlfriend that you’ve accidentally stumbled on a secret that she’s been keeping from you? And where do you go to find the right kind of play partner when online dating sites don’t seem to be doing the trick?
It’s time to gird your loins and insert coins. Let’s do this.
I’ve been seeing a girl that I met via a sugar dating website. On our first date we decided to keep it low key and simply met for coffee to chat and get to know one another. The two of us ended up talking for almost 3 hours and would have kept on chatting at the coffee shop had they not been closing and kicking us out. As we were leaving, I told her how much I enjoyed our date and that we should do it again sometime. Her reply was to invite herself over to my place where we ended up naked, sweaty and exhausted a couple of hours later.
Over the next several weeks, we texted back and forth, flirting and getting to know one another even better. Considering we met on a sugar dating website, I fully expected the time to come where she’d ask me for some financial assistance. However, every time she mentioned her financial struggles, I expected the next comment to be a request for some help. After the 2nd or 3rd time she brought up finances, I made it a point to suggest that I wanted to help her out (figuring she was too shy/ashamed to ask). She quickly said ‘no,’ because we never discussed any sort of arrangement and she felt awkward about accepting any money from me. I tried a couple more times to let her know that I wanted to help her out financially, but it was always the same reply. I sort of assumed that this meant she either a) wasn’t really into me, or b) had found another sugar daddy who was going to take care of her and it was going to be over between us. However, the flirting and chatting never stopped, just as the topic of her finances was never brought up again.
I mentioned this to a friend because I thought it was strange that a girl I met on a sugar dating website didn’t want anything from me other than my attention and affection. He figured it was because she was likely a gold digger and she’d probably either try to get pregnant or marry me. My friend agreed, however, that declining financial support was out of character for a “sugar baby” and asked if I had Googled her. Not wanting to be a stalker I hadn’t yet gone down that rabbit hole, but something about the situation now felt odd and now I had this uncertainty placed in my mind. So, I gave in and searched her name and phone number. It didn’t take long for me to find something. Searching for her phone number turned up several tweets from an account with rather provocative pictures of her under a different name. Reading the tweets nearly broke my heart, as they were exactly what you’d expect from an escort on Twitter. Most were either letting the twitterverse know she was available for “appointments,” pictures of her thanking other generous clients for their lavish “gifts,” or retweets and/or posts in support of other sex workers.
After getting over the initial feelings of shock and betrayal, I thought about it some more. She’d met me on a sugar dating website. As an escort on one of those sites, she had to have been looking for new clients. Rather than finding a new client, she met someone with whom she felt a connection and was afraid of losing out on something that might be real, so she never asked me for any money, nor has she told me about her job (like most sugar babies, she is also a college student, and I CAN confirm that).
At this point, I’m not sure what to do. I haven’t told her that I know about this yet, because I don’t want to come across as judgmental. I won’t lie, I am a bit jealous of the other guys she’s been with, but not jealous enough that I’d throw away what I have with her. I don’t disparage sex workers who have made a conscious choice to engage in that line of work (being pimped out or trafficked is another story, however). She’s obviously an active member of that rather tight-knit community, so I have no doubt that this wasn’t anything she was coerced into doing. If she were to trust me enough to come out and tell me what her job was, she’s become a close enough friend that I wouldn’t lie to her. I’d tell her that it hurts a little to know how many men I share her with, but it doesn’t mean I don’t care for her or want to continue to be a part of her life.
I just want to get this weight off of my chest. Since I found out, it’s been so hard for me not to tell her that I know, because I want her to feel that sharing this with me was done on her terms, not mine. I’ve done what I can in our conversations to try to hint to her that the only thing that matters to me is that she’s happy in the hopes that she feels safe enough to tell me herself. However, it’s getting harder each day to not let it slip that I know.
Am I wrong in my approach? Should I just tell her that I know and run the risk of blowing up something that could be great? How long should I wait for her to tell me? Or is it even worth it to keep seeing her knowing that this secret is starting to tear me up inside?
Infatuated with the Girl Next Door
OK IwtGND, I’m gonna let you in on some inside-baseball info about the dating columnist business. See, one of the more annoying parts of doing an advice column is the number of people who want to play “Look at Mr. Clever Boots” and be the first to call out “FAKE! FAKE! FAKE LETTER!”
Because apparently there are folks who think we give away no-prizes for people who want to feel very superior about having no idea about just how weird relationships can get.
Now I’ve been doing this for a while, and I’m pretty good at sussing out the fakes; most of them have some pretty obvious tells. And on the occasion one slips through…well, for the most part I don’t really care, because part of why I choose the letters I do is whether the advice can help people who are also reading along. So even if the letter is entirely hypothetical — and all letters like this are hypothetical if you’re not the one living it — then the potential for helping others who are facing similar situations makes it worth my time to respond.
Which is a long-winded way of saying: dude, there are bits of your letter that set off my Spidey-sense. Now I’m not saying you’re making things up. I know plenty of folks who’ve done various forms or sex work (more on that in a moment) and they’re not gimlet-eyed money-chasers who only see their clients as walking ATMs, nor is it as though they don’t have relationships or go on dates. But I’m not gonna lie: there are still bits that feel a bit too hinkey for me.
That being said: I like the fact that you’re being cool about her being a sex worker, and there’s a lot here about how to handle a conversation about “Hey, I accidentally stumbled over information you weren’t ready for me to have yet.” So let’s dive into it, shall we?
First and foremost, let’s look at things from her side. It’s understandable why she might want to keep this information from you. While it’s true that you met her on a compensated dating service, this doesn’t necessarily mean that you would be understanding if you found out that she was working as an escort as well. A sugar relationship is, frequently, an exclusive or semi-exclusive one, especially if it’s going to last more than a month or two. Sugar daddies (and mommies to an extent) often prefer to feel that they’re the only person their baby sees. There’s also a certain willingness to forget or elide over the financial side of the relationship; it’s easier to pretend that the allowance given is just part of their relationship dynamic. Finding out that she’s working as an escort destroys that illusion.
There’s also the fact that while, yes, you met her doing sex work, many people see a difference between sugar dating and escorting. As far as she knows, you might be cool with the possibility of giving her a regular allowance or helping her out financially, but finding out that she’s an escort might cause you to blow your top. And frankly, sex workers tend to be at disproportionate risk for violence from clients.
So it’s not weird that she might not want to bring this side of things up in casual conversation.
The next question is: Knowing what you know, what do you do about it? After all, this is information that presumably she’d prefer you hadn’t found out about.
Personally, I’m of the opinion that it’s better to let her know that you know. To be honest, I think sitting around waiting for her to trust you enough to tell her isn’t productive, and the fact that you are sitting on this secret screws with the dynamic of your relationship. The longer you go not letting her know that you’ve learned about her job, the more likely things are going to get awkward if and when she does tell you.
And then there’s also the wrinkle about how you found out. If she’s using the same phone number in her social life (compensated or no) and as an escort, this is a potential information security vulnerability that could bite her in the ass. Just as sex workers have been outed by Facebook’s photo-tagging system, her using the same number for work and play could result in her getting outed to family or doxxed by the same assholes trying to run “thot audits” on cosplayers, Instagram models and ASMR channels on YouTube.
So the best thing to do is have an Awkward Conversation. Ideally, you should have this in person, rather than over text or email. It’s hard to convey tone and nuance via text, and it’s possible that you could end up coming across upset or angry instead of understanding.
The next time you two are hanging out — preferably some place private — call out the awkward. Literally. Say “So, hey this is awkward but I think I found your other Twitter account. Everything’s cool on my end, I’m not judging you at all, I just feel weird about not letting you know that I found this.”
Then you can explain just how and why you ended up finding things. This gives you the chance to share your feelings about the relationship: You really like her, you were a little confused by the fact that she turned down the compensation that presumably was part of your relationship, and you did some googling and hey, this came up. And since you want her to trust you and feel secure with you, you wanted to let her know that you discovered this.
And then you give her room to talk. She may feel uncomfortable with your knowing. She may worry about how you feel. Alternately, she may be relieved that she doesn’t have to hide this from you and it will make her feel like she can relax and be more open with you.
Regardless of how it shakes out, remember: You aren’t judging her on this. You’re accepting her and her career without judgement or looking down on her. Don’t lie; you are a little confused and possibly feeling a bit weird. If she wants to know how you feel, you can admit to being a little jealous that she’s seeing folks besides you — even if they’re paying customers. But if you want her to feel safe and secure with you, then let her know that you aren’t bothered by her being a sex worker.
At that point, the ball’s in her court. If she needs space, then let her have some space to decide how she feels. If she feels weird about your knowing, give her what reassurance you can but let her sort things out for herself. But if you want her to give you a chance, even knowing what you know? Then you have to give her the chance to decide what she wants to do about things.
And since I know people will ask: Why won’t she accept money from you? Well, it could be professional considerations. After all, if there’s an expectation of exclusivity, then that would cut into her ability to work as an escort. She may have regular clients whose appointments help pay for college and living expenses, and the difference in income might affect her ability to go to school.
It could also be that she decided that being a sugar baby is just a dynamic she doesn’t care for. She may like the flexibility and variety of escorting vs. being a sugar baby, and it’s easier for her to refuse the money rather than have to try to change the nature of your relationship later on.
Or it could be that she likes you and wants to keep a firm line between work and her personal life. Of the friends I have who do or have done sex work, they’ve been very careful to keep a solid line between people in their personal lives and the clients they see. They may like and have genuine affection for their clients, but they need to keep those sides of themselves separate.
And one more thing: If you want to keep this relationship going, then you and she are going to be having a long series of conversations about just what your relationship would mean and what it would look like. Dating someone who does sex work can be tricky for people, and even people who think they’re cool with it can find themselves tripped up at the damndest of times. The last thing you want to do is be the guy who says he’s totally fine with things, only to demand that she quit her job for him or turn around and call her a whore when you have a fight.
Dear Dr. NerdLove:
I’m hoping this comes across as a question and not just a rant. I’m a curvy nerdy girl, and I’m kinky—wanting to be dominated/tied up/etc has been a part of my sexuality from the very beginning. For a long time I felt deeply ashamed of that, but I’ve managed to accept it (thanks in part to your article, “What Do Your Secret Sexual Desires Say About You?”).
However, I’m finding it very difficult to find someone compatible with me sexually who’s also looking for a monogamous long-term relationship. Eventually with kids. I don’t need someone whose kinks align exactly with mine, but I don’t think I could be satisfied with a vanilla-only sex life.
I’ve got OKC, Bumble, and FetLife accounts... it’s liberating to be able to be honest on FetLife, but I feel like FetLife conversation with someone looking for an LTR devolves into just sex talk (I belong to a “LTR” interest group for my city). Meanwhile, my actual name and photo are on OKC, so I don’t feel comfortable being very open about my sexuality (I do list “sex-positive” as a must). Finally, Bumble feels like a complete shot in the dark—at least with OKC, I can privately answer some sex questions and let their match % steer me towards compatible people. I chat with, and occasionally meet up with, people on those apps, but I feel like I can’t really be myself.
A big part of all of this is the whore/madonna complex, which SUCKS. On top of that, there’s a lot of judgement about kink, women who are submissive in bed, women who own their sexuality, etc. On top of even that, I’m “curvy” (I kinda prefer “fat”)... I know that many people are attracted to curvy women (fun fact: Curvy Women and the People Who Love Them is, like, the third-most-popular FetLife group), but I still don’t have much confidence in my body’s attractiveness to the average person. I still put myself out there (I often message first!), but it somehow seems relevant to mention here. For the record, I’m a US size 16, so while I’m heavier than average, I’m not a 1% outlier.
Do you have any suggestions for how someone like me should navigate dating? I can’t tell if I’m strategizing wrong or just haven’t been patient enough. I just want to be myself and find someone who’s okay with, and even loves, that person.
Have Cuffs, Will Travel
There are generally two ways people end up kinky, HCWT. Either they discovered they were kinky on their own, or they fell in love with someone who was kinky. The fact that someone may not be a kinkster now doesn’t mean that they may not develop an interest over time.
So my advice would be to maximize your chances of finding someone by not limiting yourself just to FetLife or people who list kink as one of their interests on OKCupid. Finding somebody who’s currently vanilla but is otherwise what Dan Savage calls GGG (Good in bed, giving of pleasure, and game for trying new things within reason) can expand your dating pool more than just focusing on people who are already kinky. Sometimes it can be easier to introduce kink into the relationship than to find someone who is kinky and single and your type.
Now that having been said, that doesn’t mean you should rule out kinksters. It just may be better to meet them in person than it is to find them on FetLife. See about finding some munches in your area and get to know the people in the community. It may be easier for you to connect with people in a lower-key, more informal environment than via a dating app. Since munches are explicitly not for dating, you can go with the intent just of getting to know the community you’re hoping to be part of. This way you can feel a bit more “yourself” without having to do the mating dance and putting on the performance that leaves you feeling so restricted and fake.
Plus, getting to know people in the community means you might have a chance to do some scenes, which in turn may help you feel authentically attractive and desirable.
The more comfortable you get in your own skin and your own interests, the more empowered you’ll feel in being your authentic, best self with the folks you meet up with off OKCupid or other apps. And if they prove to be decent folks who might be up for expanding their sexual repertoire…well, take a little time and break out the cuffs and blindfolds.
I’ve been reading the column for a good while now and it’s gotten to the point that I need to finally ask for advice. Let’s start with my marriage. We are incredibly close great friends. We share everything together, we have a lot of fun, so many inside jokes, love the same food and drinks, it’s a very good relationship. The sex is ok, we both work at it, but at 11 years now, it’s definitely hit the routine stage. That’s not to say we haven’t had our problems though. We are two incredibly different people. She’s an introverted pessimist and I’m an extroverted optimist. I can have fun in less than desirable situations while she on the other hand will just give up and shut down. Our couple major fights have always been about this and generally our overall compatibility.
Now here I am in a full blown affair with a coworker... Yup! It’s happened, it’s happening, it’s a thing. We have fallen in love with each other. This person is married (failing bad, divorce is imminent) with two kids. We are completely open about our situations and everything is great. Except that, my marriage isn’t really failing.
The excuses I give myself are that 1: we were so young when we got together/married (21) and I never even got to know who I was. 2: I’m extremely bored with the marriage. 3: we really are so different I find myself wanting something else. I love her although admittedly not romantically. Financially we can’t split, at least it would be incredibly difficult. Now I’m trapped in this tangled emotional mess...
Coming clean to my wife will effectively and immediately end our marriage. She’s strictly committed to a monogamous relationship, which I agreed to. I don’t want to hurt anybody but I know it will happen. What’s your take on all this?
Dazed and Confused
OK, let’s be real, D&C. Your marriage may not be failing, but you’re failing your marriage. You know this. You say this yourself: you’re giving “excuses” for having an affair because you can’t quite bring yourself to admit the truth: you want out. You just can’t bring yourself to pull that particular trigger.
I mean, it’s telling that you don’t mention things like possibly going to counseling with your wife, ending your affair with your married co-worker (which is a bad idea in general, just FYI), or trying to make things work. It’s pretty clear that you’ve got a foot out the door and you’re waiting for someone to give you that push.
C’mon. The only options you’ve brought up are continue and hope you don’t get caught…or tell your wife and get divorced.
But there’s a third option: You get a divorce and don’t tell your wife about your affair.
Now, maybe you don’t feel like things are “bad” enough to divorce. Maybe you are afraid of the disruption to your life, the “difficulties” of disentangling yourself financially, the judgement of others for leaving your wife.
But you can leave any relationship at any time, for any reason. And wanting out is a legitimate reason. It may not be one that many people will accept or agree with or think is a good one, but it is legitimate.
And to be blunt: As tricky as extracting yourself may be right now, it’s your best option. Continuing your relationship(s) as they currently stand is going to end in pain for everyone — for you, for your wife, for your co-worker and her family. You’ve chosen a way out that’s going to detonate, messily and all over the place.
Accepting that you want out and ending your marriage — without the needless, extra pain of admitting to your affair — is the quickest, cleanest option you have. It’s going to hurt. There’s no avoiding it. You’re going to hurt your wife by doing this. But this is a quicker, cleaner pain than drawing things out by pretending to still be committed and the inevitable ugliness that will result. And it’s possible — remote, but possible — that you could maintain a friendship with your wife by leaving now. That emphatically won’t happen when you get busted for having an affair.
So do yourself and your wife a favor. Start talking to a lawyer and get ready to untangle your finances. It’ll be better for all of you in the long run. Because at least this way, you’ll be leaving under better terms than getting found out and thrown out.
Did you ever have a sugar baby/daddy relationship? Did you help a vanilla partner discover a love of kink? Share your story in the comments below and we’ll be back with more of your questions in two weeks.
Ask Dr. NerdLove is Kotaku’s bi-weekly dating column, hosted by the one and only Harris O’Malley, AKA Dr. NerdLove. Got a question you’d like answered? Write [email protected] and put “Kotaku” in the subject line.
Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove YouTube channel. His new dating guide New Game : The Geek’s Guide to Love, Sex and Dating is out now from Amazon, iTunes and everywhere fine books are sold He is also a regular guest at One Of Us.
He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.