DEAR DR. NERDLOVE: First of all, sorry if I have mistakes or my grammar is not perfect, I’m from Spain and English is not my main language.

I’m a 28 year old man and I’m in a relationship with a 27 year old woman. We have been dating for almost 9 years and we are planning our wedding for next year.

The thing is that I like to have butt play, like pegging or a finger up my butt. I have talked about that with my girlfriend and we tried pegging and some butt play, but it’s not as frequent as I would like. We talked about that a few times and I let her know that I would like more initiative from her on doing that stuff.

I know she does that things to please me, and if I ask she will give it to me. The problem is that I get embarrassed to ask for that because I feel like she will not enjoy it or she will prefer vanilla sex (every time we did pegging is because I asked for it, this year maybe we did It like 6 times).

Just need another perspective about the situation. Is there something I’m not considering about her feelings? Should I just talk to her about how I feel? Is it normal to be embarrassed on ask for something I like?

Bend Over Boyfriend

DEAR BEND OVER BOYFRIEND: Let’s work from the bottom up, BOB. Er… as it were.

To start with: being embarrassed about asking for something you like is common, yes. But there’s a difference between something being common and being “normal”. Normal would imply that there’s a legitimate reason to be embarrassed, that you’re doing something that’s unnatural or forbidden or shameful, and you’re not. Anal play and the various acts you enjoy are none of those. There is a lot of cultural bulls--t around butt play, driven primarily by homophobia and toxic ideas about men and male sexuality, sure… but that’s the province of insecure a--holes. Life is too short to consider the opinions of a--holes.

… yeah look these are just gonna keep happening.

You, BOB, are a man who knows what he likes, and what you like includes anal play. Asking for it from your partner can be embarrassing because of those cultural narratives, sure… but the more you embrace it as part of who you are and see it as just one more form of sexual pleasure can help you overcome that feeling that you’re asking for too much, or something that you shouldn’t want.

Now, let’s talk for a moment about asking your partner for more anal play and how she feels about it. The big question is: is this something that she could get in to, something that she could take or leave, or is it an act that’s going to leave her feeling violated or freaked out over and have her sobbing in the shower afterwards? I assume that if it were the latter, you would’ve said so, so let’s work from the assumption that she’s more or less neutral on it. Maybe a little squicked out at the idea of possibly encountering some poop if she puts her finger up you, but otherwise it’s neither something she loves nor loathes.

Here’s my general philosophy on sex: sex is best when both partners are what Dan Savage calls “GGG” or “good, giving and game”; that is, they’re good or skilled in bed, giving of pleasure and game for trying things that they may not be into themselves… within reason. The “within reason” part is important; after all, the last thing you want is for your partner to feel like they’re sandpapering their soul while in bed with you.

However, the “being up for trying things for the sake of your partner” part is actually an important part of relationship satisfaction and stability. Not, mind you, because you’re getting what you want in bed, but because it makes you (or your partner, if you’re the one being game) feel heard, understood and valued. You (or they) are doing something that you may not get a charge out of, but because you know your partner does. It’s a little like making the little gestures that don’t mean much one way or the other to you, but mean the world to your partner. It becomes a way of reaffirming that you love them and want them to be happy and satisfied.

In your case, this means a little more anal play during sex… which I don’t think is that big of an ask, all things considered, especially since you’re the one asking to be penetrated.

I think it would be good for you and your partner to sit and have a slightly modified version of the Awkward Conversation. What you want is to talk a little about your sex life, how she feels about things and how the two of you can make this work in a way that is amenable to the both of you.

This may mean making sure that your anal hygiene is top-notch – making sure you drink plenty of water, get plenty of fiber, possibly add a bidet attachment to your toilet for extra cleanliness and butt health. This could help ease any inherent “ick” she’s feeling regarding touching your anus or prostate. Or it may require some compromising and some out-of-the-box thinking, depending on circumstances.

You might, for example, find that adding some digital play during foreplay or penetration to the regular sexual repertoire, while pegging might be more infrequent – not a “just on my birthday and Christmas” schedule but maybe not every time you two have sex. There may be times, for example, where she may not feel like being penetrated, but is down for penetrating you instead. Or you might try getting a butt-plug and wearing it when the two of you have sex; this way, you get the prostate stimulation and feeling of penetration during sex, but you partner doesn’t need to be the one trying to keep the dam from leaking. Just make sure that you get a plug with a flared base; the last thing you want is an awkward trip to the emergency room to try to fish it out.

However, as I said: the first step is to work towards not being embarrassed to ask for what you want or need. This is just another form of sexual pleasure that you like to indulge in, that’s all. There’s nothing weird or unusual about liking butt play; prostate stimulation can feel incredible, whether it’s internal or externally stimulated. Similarly, you should be able to talk to your partner about this; if you can’t talk about the things that bring you pleasure with the person you’re planning on spending your life with, who can you talk to about it?

Just don’t forget that turnabout is fair play. If there’re things your partner likes in bed that you’re not necessarily into, providing them for her with willingness and good cheer is fair and contributes to the overall strength and happiness in your relationship overall.

Good luck.  

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DEAR DR. NERDLOVE: So I had to tell a girl I went on a couple of dates with that I couldn’t be friends with them anymore, and I’m just wondering for feedback on the whole situation.��So essentially, I had met this girl through my friend in grad school, and we had hung out a couple of times in a group, and I kind of suspected that we were both interested in each other, but I wasn’t sure if it was something I wanted to pursue for a couple of weeks. Eventually I decide to DM them on Instagram, and we text for a bit before they tell me they’re going to come to a Halloween card game night we have planned. Our mutual friend had given me advance warning on a couple of things: They were talking to another guy, they had just gotten out of a year-long relationship, and that they weren’t sure they wanted a relationship and weren’t in a great place right now.

They come to the board game night, things are obviously really flirty between us, and I ask them out at the end of the night, to which they say yes. They come off very affectionately over text over the next week before the date and they text me a lot beforehand, which I’m unsure about at the time. They also give me advance warning that they’re stressed with school, so if they seem off on the date, that’s probably why, and ask if we can study at my place after. I say okay.

We go on the date, and it goes pretty well, and things go to my place eventually and we start making out, but they don’t want to have sex because “they don’t know what they want from this yet, and they don’t want to hurt me”. I’m fine with the not having sex bit, but the other two are kind of making me nervous. They’re also staying the night at this point, because I offered. After they stay the night, they go back to their place, and we potentially have a second date in under a week (because they’re not sure they’ll be in town for our grad school with a bus strike going on). However, over the week, their texts start drying up and they’re not letting me know if they’re going to be in town, and so I assume they’re cancelling. They do mention that they’ve been having a rough few days with mental health issues, but it kind of looks like I’m getting the fade. ��Eventually, on the day of, they tell me they’ll be in town and they’re still good to study that night, which I agree to. Eventually, when they come over, we chat for a bit, but they tell me that they’re not doing as well as they thought they were post-breakup, and they didn’t want to lead me on and think they could give me what I wanted (my friend had told her I wanted a relationship). However, they’d like to be friends. They were also going through a depressive episode and had just gotten out of a string of long-term relationships. We talk about their episode, relationships and I connect with them over also struggling with mental health stuff. It’s still quite flirty, but I do say that after that night it can’t be like that anymore. They also say that they’re still talking to the other man, but it’s because they’ve known them for a lot longer, and it’s like, whatever, not my business.

Eventually, they leave, and they start texting me again, and they say they want to go to a card game night I was planning, but they had a breakdown after their class so they might not be able to with all the work they have, and that they were “thinking of texting me during to ask if we could talk (we have class in the same building) but they knew I had class and didn’t want to overstep”. I say it’s fine, I’ll let them know if I think they are.��Night of, they ask if they can come over early because they’re spiraling and want a change of scenery. I’m in a café close to my place at this point, but I’m probably heading back soon and I say sure, when do you want to be there, and they start saying “it’s okay, I don’t want to bother you” and after reassuring her it’s fine, she comes over. She’s doing better now and we just talk for a half hour before everyone else arrives, and things seem cool. During the board game night, they start texting me, and given that they had mentioned previously they were stressed, (they’re texting me “:C”) I’m wondering if they’re okay. They say they are, and it’s nothing bad but “they don’t want to say it”, before calling me cute and telling me they “wanna be dumb” (they used this to refer to us having sex on our date). I’m very caught off guard, and a while later, I respond that it’s mutual and ask if we can talk after.

When we’re walking to the bus, I clarify that she meant what I thought, and basically ask her stuff along the lines of, “what do you want from this”, “why would you say this if you don’t want anything”, “it’s not cool to tell me we’re just friends and then say this”, and she responds that she’s sorry, knows it wasn’t fair, didn’t think it’d have this effect, yada yada. They also mention that “they’re used to being treated as disposable by dudes, so they didn’t think I’d care this much” (Apparently they have a not great relationship track record but I’m not sure if they’re feeding me a line), and that “they felt connected with me after we talked about our experiences with depression, and when I added two women to our social circle’s group chat later, they felt really jealous”. They also still clarify that they don’t want anything. Eventually, that night, we call, I ask if they’d be interested in a casual relationship, they say “no”, I say okay, but I talk with my friends about what happened, including our mutual friend, and I’m basically warned that this person is in a self-destructive phase in their life, in a very bad place, likely using both me and the guy they’re talking to for attention, and that they’re “a toxic time bomb”.

The one caveat is that even though the mutual friend did kind of set us up, they were at one point a couple of months ago attracted to me, but I didn’t pursue them and I’m pretty sure they got the hint. After a lot of deliberation, I tell them we shouldn’t be friends right now and that I’d like to reconnect later. They say they understand, are really sorry again for what happened, before they proceed to block me.��I’m just wondering if I did the right thing with them, I guess. I feel bad for wanting space from them, but I also feel that I was in a really weird situation, and that they wanted a weird substitute boyfriend instead of a legitimate friend. As well, literally everyone I talked to about this told me they were acting really weird and this was for the best.

Thanks,�Hot then Cold

DEAR HOT THEN COLD: Let me put your mind at ease right of the bat, HTC: you did the right thing. You did what a lot of people need to do when it comes to situations where someone seems to be cycling faster than my washing machine: you prioritized protecting yourself, rather than assuming that either you could ride this out and get something out of the situation or that you could somehow “fix” them.

I have a lot of sympathy for folks who are having hard times with mood swings, depressive cycles, manic episodes or other issues that make life difficult. In some ways, it can feel like the ultimate betrayal; your brain is what’s regulating all the systems of this meat mech suit you pilot, so you’d think it would at least do you the courtesy of being on your side. But often it isn’t. And while we’re all messy piles of electrified tapioca, there’s being in good working order and not being in good working order. From what you describe, it sounds like your friend was very much in the latter category.

The important thing here, however, is that your friend’s mental health or stability isn’t your responsibility. You’re not their doctor, father, brother, counselor, priest, confessor or anyone else with a remit and responsibility for them. You’re someone who’s just looking for a friend and maybe a relationship. As much as you may or may like that person, you do have an obligation to yourself and your own interests. It can feel selfish, I know, but you aren’t able to help them nor do you have the resources to do so. Trying to do so would not make things better, have a strong likelihood of making things worse and likely harming you in the process. There are reasons why we tell people that they should put their own oxygen mask on first before helping other people with theirs, after all.

Similarly, this person was not in a position to give you what you need, either from a friend or from a relationship. You want stability and certainty and a partner who actually knows what they want. Your friend couldn’t provide any of these things, and what they do offer shouldn’t be accepted. While I won’t say they weren’t in a position to consent when they changed their mind about maybe possibly hooking up with you, I do think that there was a very strong likelihood that sleeping with them would’ve been a bad scene for everyone involved. They may have wanted it in the moment, but that doesn’t necessarily mean that it would’ve been healthy for them at that time – especially when your relationship was very much in flux. So I’m glad that you chose not to go through with things.  

Now, I don’t know this person, and I certainly don’t know your friends and their relationship to them. I can’t say whether this person was being a toxic timebomb or using you for attention or what. I suspect that they weren’t sure about what they were doing or what they wanted and were going with where the winds and their swings took them. But either way: this would’ve been a bad things all around, and you were right to say “I can’t do this and I need to step away”.

So, as the man once said: you chose… wisely. Getting space and putting up boundaries was exactly the right thing. You have to be your own biggest fan and strongest advocate for your own needs and safety and that’s precisely what you did. It’s a shame that you had to do this and I know you’d have preferred to not be in this position. It was uncomfortable and awkward and you did it anyway and that’s admirable.

Rest easy, HTC, because this was the right call all around. You used your words, made sure you and they understood each other and ultimately recognized that this was not going to be a relationship, platonic or otherwise, that would have been good for you. There will be more opportunities in the future, with people who are in the right place at the right time for both of you. Letting this go was the right thing to do.

Good luck.

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DEAR DR. NERDLOVE: I hope you’re having a good holiday season. In fact, that’s why I’m writing to you: I don’t want to ruin the holidays with my issues. So here’s a quick run down of my backstory: my boyfriend (m/25) and I (m/25) have been together for two years, and he’s incredible. We’re very much in love and have a great relationship. However, there’s one significant issue: his parents.

This Christmas, like the last, I’m invited to spend the holiday at his parents’ house. The problem is, I really don’t like his parents. They’re not bad people, and they’ve always been kind to me, but we’re just fundamentally different in many ways – our interests, beliefs, and even sense of humor don’t align. At the risk of sounding snotty or snobbish, they’re not really cultured in the way I am, and they don’t get or understand a lot of the things I enjoy, and so we never quite understand each other. It’s almost like we’re talking two entirely different languages, with different cultural idioms, references and views of the world. It’s not for lack of trying, but there comes a point where even well-meaning and earnest attempts to connect just fizzle out and we’re all left just staring at each other with an increasingly awkward silence. This makes spending time with them exhausting and often uncomfortable for me.

I want to be clear: his parents are lovely people. They had some issues adjusting to learning their son was gay at first but they’ve been the sort of “show-up-at-Pride-parades-with-snacks-for-everyone” supportive types and if they get something wrong, they’re quick to apologize and try to get it right. They seem to genuinely like me and are always excited when I visit. My boyfriend adores his parents and is oblivious to my discomfort and I honestly would prefer to keep it that way because it’s my problem to solve, not his. He’s thrilled about spending Christmas together as a family and all their little traditions and I don’t want to disappoint him or create tension.

I’m torn between my love for my boyfriend and my discomfort around his parents. I want to be supportive and participate in his family traditions, but the thought of spending an extended period with his parents fills me with dread. How do I handle this situation without hurting my boyfriend or damaging our relationship?

Sincerely, Homesick for the Holidays

DEAR HOMESICK FOR THE HOLIDAYS: I’ll be honest, HFTH, I read your letter and I’m picturing Niles Crane trying to get through Christmas in Biloxi, Mississippi and quietly dying because he’s going to dinner at Applebee’s or something. And while admittedly it’s an amusing image, I feel like that might be an apt description of what’s going on here and, thus an entry into the problem. 

In fact, based on your description of the situation, I wonder if this is a sort of city mouse/country mouse situation or awkward Hallmark home-to-the-small-town scenario where the big city boyfriend just can’t grasp the virtues of small town life.

(And TBH, as a dedicated city rat, I always feel my hackles rise a little during those movies. I swear I’m going to write a Christmas movie about someone stuck in the Bronx for Christmas and learning the joys of diverse communities, big-city conveniences and identities based around shared neighborhoods…)

It’s the sort of thing that feels a little like class snobbery, but also a little of the idea that the urban/rural divide is somehow so diametrically opposed to one another – a cultural oil and vinegar, of sorts – that the two can’t really blend without a lot of agitation in the process. And again, it’s a gift for someone trying to come up with a suitably pithy metaphor, but I think it speaks a little to mindset and where the actual problem lies. Not in your boyfriend’s parents so much as in how you see him and where he came from.

I bring this up, in part, because I wonder just how much of an effort you’ve actually made at meeting the parents where they’re at and how much of the barrier you’re feeling is the sort of snobbishness you say you’re trying to avoid. If you’re seeing his family as provincial or less sophisticated or enlightened, I can see a sort of mindset of “well of course my boyfriend can bridge this gap, our superior culture was what he was missing but I’m having to dial myself down to be at their level” coming up. This kind of thinking leads to situations like yours, where you’re physically present and participating but still holding yourself back. A sort of “I’ll do this because I have to, but I know I’m better than this” sort of attitude.

In fact, I see this happen in a lot of relationships in general, where someone will make a half-hearted attempt at participating in something their partner finds important but they find a little distasteful or that’s beneath them in some way. This is less “sharing in my partner’s interests” so much as touching a base (under duress) and doing as little as possible to still get the credit for being involved at all. In times like that, it’s almost better to say “hey, you do your thing with your friends who are also into it and we’ll meet up afterwards.” This way, at least, they don’t have to devote any mental or emotional bandwidth towards worrying that you’re not enjoying things, bringing down the group’s fun or otherwise trying to play cruise director while finding ways to keep you engaged.

However, that approach is a little harder to do during a holiday trip to see the fam. It’s definitely hard to do that without coming across as a little rude or stand-off-ish. So I wonder if, perhaps, even as you go and “participate”, you’re holding yourself back; you’re attending more as an anthropologist observing others from an elevated, outsider’s perspective, rather than someone who’s actually fully involved. This is the sort of thing that a lot of folks think they’re managing to hide, but it comes across in the way they behave. There’s a begrudging sort of “ok, fine“, that bleeds into your body language and overall attitude.

Since it doesn’t sound like you’re being asked to do or tolerate things that would be harmful or unpleasant (say, going to Christmas services in a very homophobic church), I wonder if maybe the issue is that you don’t actually commit and let yourself enjoy them. Is it possible that you’re holding back and approaching these trips with a level of detachment or irony for fear of… I dunno, losing some sense of cultural superiority? Is it possible that the simple sincerity of something you see as being more provincial or what-have-you strikes you as being a bit cringe?

Perhaps, for this Christmas, a gift you could give yourself would be that, instead of avoiding cringe, you cut out the part of yourself that cringes and just try connecting with the sincerity of it. Instead of thinking of your boyfriend’s family traditions as being less cultured, less sophisticated or whatever, you try letting go and just trying to enjoy it for what it is. If it helps, think of it as inhabiting a role; at first, you’re going through the motions, but as you relax into it, you may find that you enjoy it more if you don’t have your guard up.

The same goes with connecting with his parents. It sounds like they’ve been making an effort to reach out to you; perhaps it’s time to return the favor and try to reach out and try to appreciate things from their side of the divide. You may even find that it’s a little easier to start before you go, where it’s a little easier to explore their cultural milieu, knowing that your comfort zone is within easy reach.   

Failing that, perhaps the way to get more comfortable is to connect with the way it brings your boyfriend joy. It may not be your favorite flavor of eggnog, but it’s his and if you can zero in on that and the joy of seeing him come to life with all the cheese and tinsel-covered glintz and gingerbread. You might even be able to find aspects of it that are more refined or complex than you’d previously expected.

The big thing to hang onto is that while you may not necessarily dig his family or their traditions, you can at least respect them and be a full participant. Even if you’re not having the bestest of the best times, is this something that you can manage for him, at least occasionally? Perhaps a compromise here would be, as is with so many couples, to alternate years – even years you visit his family for the holidays, odd ones you visit yours… or even have years where you bring the families to you. You might even be able to share (or start) some traditions of your own with his family… even if it’s just annual viewings of The Hogfather or Anna And The Apocalypse.

But, at the very least, give it an honest shot at letting your guard down and just trying to lean into the spirit of the thing. If you give it a couple of sincere attempts and it just doesn’t work, you can focus on the “at least respect it if you can’t enjoy it” aspect, if only for your boyfriend’s sake.

Good luck.

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Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com