DEAR DR. NERDLOVE: This isn’t so much a romantic issue as it is a dealing with a jerk issue.

My sister befriended this guy that she talks to almost nonstop. They call each other every day, and talk for several hours at a time and from a distance it seems like they have a great relationship. However, when she starts talking to me about this guy in detail I get worried.

Based on what I’ve heard he has jealousy issues, holds no respect for my sister, and he doesn’t seem to hold the word no in his personal vocabulary. Just today they got into an argument because this dude kept trying to pressure my 18 year old sister into agreeing to let him impregnate her and she wouldn’t stand for it. His reasoning was that he wanted her pregnant so that other dudes wouldn’t look at her. The other day they got into a fight because he wanted her to give him anal sex and she blatantly refused. When she tried to flip the script on him and asked “How would you like it if I shoved my finger up your ass when you didn’t want me to?” He responded, “It’s different for you because you’re a girl.”

In addition to that, whenever HE decides their arguments are finished he’ll merely agree to whatever she says in an effort to shut her up, not because he genuinely believes and respects her opinion. He’s also prone to making false promises for changed behavior but he never follows through. This is deeply troubling behavior for me to witness. If it were me, I would dump him like a sack of bricks, but it’s not me it’s my sister and she still wants to maintain contact with this guy. How can she better navigate their relationship without feeling like she’s walking on landmines all the time?

Sincerely,

Worried and Frustrated

DEAR WORRIED AND FRUSTRATED: These are the kinds of letters I hate getting WaF, because there’s on reasonable way to grab a stranger by the scruff of the neck and shake them until the stupid falls out. Because, um, HOLY HOPPING SHEEP S

T this isn’t a man, this is horde of red flags in a trench coat. This guy is waving more red flags than a military parade in Tiananmen Square and the best thing your sister can do is dump this guy so hard his grandparents get divorced retroactively. She should be NOPE-ing out of there so fast she leaves a human-shaped cloud behind as she hopes the Nope Train to F

k This S

tville.

You know this. I know this. The problem is that your sister doesn’t seem to get this and short of strapping her to a chair and giving her the full Ludovico Technique, you can’t force her to see it. And since your sister is a grown-ass woman and you’re not her legal guardian, you can’t exactly force her away from him.

Not that this would actually work, mind you. There’s no narrative as compelling to young, naive lovers as “nobody understands him the way I do!” Once they gets the feeling that everyone’s against them and their love, it quickly becomes a “you and me against the world” scenario and I can tell you from experience: that’s more likely to make them double down as it is to make them see sense and break up.

Which makes your handling this tricky. You want what’s best for your sister, but you also don’t want to give this your blessing or your approval just because she’s determined to make her own mistakes.  But just pushing her about how awful this guy is can be a great way to push her into his arms and away from you. As much as I hate to fall back to cliches and song lyrics, when people’re in love with someone (or near as dammit), they can do no wrong and like as not, they will turn their back on someone who puts ’em down. As much as we all wish we could, we can’t force someone to see how much of a s

tbag they’re dating.

But you can lead them into seeing it. Sometimes.

The trick is that it they have to feel like they’re the one who came to that conclusion. There’s no argument more powerful or persuasive than the ones that people come up with themselves. You just have to guide them to it.

So the key is that you need to talk with your sister. You can start this by expressing concern… it sounds like they’re really fighting a lot and the things he’s asking for are incredibly unreasonable. Why does she think he keeps demanding things like this from her? Is it really her responsibility to control other people’s thoughts or reactions? Isn’t it frustrating that he never seems to take her “no” as a “no” instead of the start of a negotiation? Is she ok with all of these demands he’s making on her? Is she comfortable with the way he reacts when she turns him down? She knows that it’s not cool for him to keep pushing after she’s said “no” to something, right?

The odds are good that she’ll come back with a litany of very common responses. “It’s not that bad.” “He doesn’t mean it that way.” “It’s not like he’s serious.” The key here is that you don’t argue with her. You aren’t trying to contradict her sense of reality; that’s more likely to make her double down on her claims that she’s fine, it’s fine, everything’s fine, it’s fine. Instead, you express concern: “Well, it’s just that the last few times you’ve been talking, you’ve been arguing.” “I just worry because it seems like when you’re talking to him, you turn into a different person; it’s like you’re tiptoeing on eggshells around him.”  Rather than asking her to agree with your facts, ask her to agree that your worries aren’t unfounded: “OK, but looking at it from my end, we can agree that it’s reasonable that I might see it that way, right?” You aren’t challenging her facts, you’re just asking her to agree that you’re both reasonable, rational people and that as a reasonable, rational person, your interpretation of things isn’t out of line.

Then you want to reassure her that you’re just worried about her and for her and that you care. Remind her that she shouldn’t let him push her into something she doesn’t want to do and that you always have her back. Emphasize that you two are on the same team and that you are always going to be there to listen and provide support if she needs to talk about things or is feeling weird about stuff.

And then you just make sure that you keep the lines of communication open. She may not necessarily be receptive to this immediately, but by keeping things non-confrontational and supportive,  you help encourage her to come to you when she does start feeling hinky about this guy.

You’re not likely to change her mind overnight, and you shouldn’t expect to. This is more about planting a seed that will hopefully grow into awareness… hopefully sooner rather than later.

Now the thing I would suggest you do be firm about is that she get on some form of semi-permanent birth control… something that he can’t undo or sabotage. Condoms “break”, birth control pills don’t always work and you can be talked into not taking them. An IUD or a hormonal implant (or even Depo-Provera) are all things that he can’t f

k with. Offer to take her to the doctor or Planned Parenthood yourself. Offer to pay for it, if that makes the difference. Even if you have to frame it as “this way you can’t have any accidents”, it’s really important that she not be in a position to “accidentally” get pregnant with him. A lot of abusers will use pregnancy to force their partners into compliance and denying him this chance makes it that much easier for your sister to get the cinnamon toast F

k away from him. And even if he’s not an abuser, just an asshole… the last thing she needs is to be scrambling her DNA with this s

theel.

You’re a good sister, and hopefully you can get your little sister away from this dude with the quickness. But keep in mind: what she needs more than anything else is your support, not your judgement. She won’t leave him before she’s good and ready, and knowing that you’re there willing to provide the love and support she’ll need can be a huge motivating factor.

Good luck. And write back to let us know how it’s going.

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

DEAR DR. NERDLOVE: I’ve been listening and reading your works for a while now, and I have found your insights and advice really helpful —and your obvert feminism and repudiation of pseudoscience wonderfully refreshing, considering what the standards of the industry sometimes seem to be.

I am a 27 year-old straight male that, one year after a friendly break-up that I’ve spent working on self-improvement, feels ready to get back on the dating wagon.

Some weeks ago I met a girl at work whom I found instantly attractive. I got her number and, after another random meeting at work, started messaging her the next two weeks, during a holiday trip she took. What started as simply making sure that my interest was noticed (so that we could maybe meet after her holidays) turned quickly into daily conversations, and soon after into hardcore flirting by both of us.

She proposed to meet the day after she was back, and ended up spending about 10 hours together, from the early afternoon until after midnight. Everything felt natural and clicked, the sexual tension was palpable, and before the date was over we were making out passionately. All in all a wonderful experience.

Thing is: a few days later we met again, and this time she suggested bringing some friends to the meeting. The night was fun and all, but I didn’t feel there was an appropriate time to make out again: no intimate time, no time just the both of us; still, the chemistry was there, so I didn’t make a great deal of it.

Fast forward to a few days ago, when we met alone right before she went again on a trip, and had the conversation I feel really confused and want to ask you about.

She wanted to talk about how she felt about us, and told me that while on the one hand she felt attracted to me and really enjoyed our conversations, and thought we clicked together, on the other she wasn’t sure about wanting to pursue a physical relationship at the moment. She added that there had been times in her life when she felt pressured by the expectations of others to become physical or sexual with other men even when she wasn’t too sure about it, and didn’t want to experience that pressure again. She also said that she was seeing other people, and really didn’t contemplate the possibility of an exclusive relationship for the time being. She enjoyed everything that had happened so far, and didn’t find any fault with me or my doing.

Much of this didn’t bother me: I don’t know that I want anything serious yet, I’m seeing other people too, and, although I’m REALLY attracted to her (sexually and as a person, and I made sure to state this clearly), I’m nowhere close to infatuation.

The question is: should I assume that she’s not really sexually interested in me (her relatively convoluted way of saying that being simply a stylistic choice) and move on? That being the case, how does that make sense after such a (and I really, really don’t think I’m misreading this) passionate and wonderful date, preceded by unmistakable flirtation and followed by what seems to be a genuine interest to see me again and maintain some form of an active relationship (albeit perhaps a non-sexual one)?

The entire story spans only a few weeks, and it ending without getting any further wouldn’t be tragic, but I’m intrigued by what appears to me as an erratic behaviour or inscrutable expectations, and perhaps there is a transcendental truth I’m not seeing to be learnt from this experience.

Not Sure I Understand People

DEAR NOT SURE I UNDERSTAND PEOPLE: I’m gonna help you out here, NSIUP: the transcendental truth to be found here is… literally what she told you. She’s not ready or interested in a physical relationship. More specifically: she’s not ready or interested in pursuing one with you.

A lot of times, after having been on a couple of dates — some times even just one date — people who just aren’t feeling it will do the courteous thing and tell you. And since they don’t want to be harsh or make you feel bad about it, they’ll often add a softener, something that’s meant to take the sting out of it. And since rejection always feels personal — and some dudes really react badly to being rejected — they’ll phrase it in a way that makes it less of a rejection and more of an obstacle that just can’t be overcome. This is why folks will say “it’s not you, it’s me” or  “I’m just not ready to date.” It’s a shame, if circumstances were different then you two would have a chance but they aren’t, so you don’t. Oh well, what can you do, the stars are aligned against us, nothing to be done about it. Occasionally they’ll even add a “right now” to this because, well, it’s not like they’re going to be single forever.

The problem is that while people will do this as a kindness (or occasionally as a way of not getting murked), the people hearing it don’t quite understand what’s actually being said. That’s why when someone says something along the lines of “I’m just not ready to/ interested in/ able to have a relationship”, you have to silently append the unspoken “…with you” to the end of it.  Otherwise you run the risk of giving yourself false hope (or in some cases, ignoring the screamingly obvious) and holding onto the “for now” instead.

Once you start recognizing this, then it’s easier to start working out just what happened.

Let’s look at what happened with you and your friend, NSIUP. You had a lot of chemistry over text, when you met up you had an amazing date that ended with crazy make-outs. All well and good. But the second time you got together, she invited some friends to come too. That in and of itself is… not a warning or red flag, necessarily, but it’s definitely an indication that she wants to ensure that sex or any physical tomfoolery was on the table. That’s something that folks will do when, say, they suspect that their platonic “friend” just invited them on Schrödinger’s Date. So by this point, your friend was sending up a flag of some sort.

The conversation you had afterwards, about how she didn’t want to pursue a physical relationship with you and how sometimes she felt pressured into getting physical when she didn’t want to gives further clarity to her mindset here. This, for example, tells us that the odds are good that her friends were as much chaperones as they were invited to share in cool goings-on.

Now, the interesting part is that she mentions that she’s also seeing other folks. While this could be taken as “so don’t be surprised if you see my relationship status change”, it could also be an indicator of just why she’s telling you this.

So keeping in mind that I’m not a mind reader and the only person who really knows what this all means is her, here’s my best guess at what went down.

You all had a great date… but somewhere along the line she either started feeling weird about things or she started having questions about where this was going. Things may have moved faster than she was necessarily ready for. She may have caught a vibe that you were more into her, and had more expectations, than she was into you. Something you may have said or done may have given her the impression that you wanted more from her than she was ready to (or able to) give. Or that the make-outs on the first date were nice, she wasn’t quite feeling it as much, and wanted to make sure that there wasn’t any awkward “no, we’re not gonna this time” on the second get together.

And then she had the “It’s not you, it’s me” conversation with you and here we all are.

One thing I want to point out: as harsh as this may sound, she’s actually paying you a compliment by having this conversation with you. She was making a point of doing you the courtesy of turning you down in person and respecting your time by being fairly upfront about things. Those are all generally good signs. A lot of folks would just ghost on you or pull the fade.

But over all: you were feeling it. She wasn’t. You two may not have been right for one another, you may have been at incompatible places in life or there may have been some crossed wires. But at the end of the day, both people have to want to turn the key and she just didn’t.

Unfortunately, the best thing you can do is take what you’ve learned here and apply it to your next date.

Good luck.

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

DEAR DR. NERDLOVE: Short and sweet. I just want to know how unhealthy it is that my girlfriend continues to be friends with all these men that openly want to have sex with her.

Concerned

DEAR CONCERNED: Normally, this is the sort of question I’d pass over because there’s pretty much nothing here and one that usually gets a snarky one-sentence answer. But I decided to feature this one because, frankly, I get this question a lot and honestly, in a lot of cases the details don’t matter. Yeah, there’re questions of “have they actually said ‘Hey, Concerned’s Girlfriend, I want to part you like the Red Sea and plow you like a field’ or are you assuming this?” and “Have you talked to your girlfriend about how you feel?” but at the end of the day, this comes down to one singular issue:

Trust.

Either you trust your girlfriend or you don’t. That’s really it.

See, one of the things that everyone is going to have to get over is the idea that other people are going to want to f

k their partner. Some of those people may very well be their friends. Hell, those people may well be their close friends. Some may be secretive about it, never letting on that deep in their minds, they fantasize about getting some intense crotch-snuggles with your sweetie. Some will be faking being their friend in order to get there. Some will be quite open about it. And while it’s important to be open with your partner about how you feel about such things – letting them know that you might be feeling a little uncomfortable with the level of intimacy the other person is assuming or asking for, f’rex – the thing you need to keep in mind at all times is very simple:

It takes two to horizontal tango. Or to mambo with the mamba. To bring the Ark into the Holiest of Holies. To be banged in the butt by the Space Raptor Invasion.

So at the end of the day, the fact that dudes may line up for miles in hopes of getting into your girlfriend’s panties, Concerned, it doesn’t matter because no matter how much they may want to raid her tombs, it ain’t going to happen unless she wants to f

k them as well.

And don’t get me wrong: the fact that she’s hanging out with dudes who want to f

k her isn’t an indication that she is planning on – or wants to, or has even thought about – f

king them. Maybe she doesn’t know. Maybe she does and is willing to overlook things because he’s not an a

hole about it or because their friendship has always been flirty and that’s just their dynamic, or she knows and really wishes he’d drop the subject because otherwise he’s a decent guy or she knows but he’s never said anything so she’s willing to pretend she doesn’t know.

Now, maybe she does know and likes stringing those guys along. In which case the problem isn’t her friendship with those guys, it’s her personality, and you’re better off breaking up with her because Jesus, who wants to deal with that bulls

t? But the likelihood of that is so damn rare that you may as well buy some scratch-offs while you’re at it because if you beat those odds, you might win $75,000 at the Circle-K.

But back in the world where women aren’t conniving, Machiavellian schemers who mostly exist in the fetid and fedora’d imaginations of guys who they’d never date in the first place…

You don’t get to dictate who your girlfriend is friends with or under what conditions she’s able to be friends with them. Either you trust her, or you don’t. If you do trust her, then it’s on you to use your words like a grown-up and ask for a little reassurance from her because right now you’re feeling a little insecure and you’d appreciate it if she could help walk you back from the edge. If you don’t trust her, then it’s time to break up with her.

DEAR DR. NERDLOVE: A few years ago I met a guy. I thought he was cute and we were both socially awkward. Two years ago we had an awkward make out session and that was the end of the crush, but we’re still friends.

I noticed after the make out session that he started getting kind of weird. I am pretty sure he’s a closeted transgendered individual. I kind of brushed off the signs like him always identifying with the female protagonist and his favorite shows being about people who felt like they were born in the wrong bodies.

Last year we went to a fan convention and he decided to dress up as a female character. When he asked me if he should do it, I told him to do whatever made him happy. I didn’t realize that by telling him to do what he wanted that it put me on the hook for having to emotionally support his decision.

He spent the entire convention making me do his hair and makeup. He asked me every five minutes if he looked pretty. He wanted to obsess about how his bra made him feel and how to avoid showing his underwear when he leaned over.

He also started a fake Twitter account where he pretends to be a girl. He will contact me to gleefully tell me that some guy is flirting with him because they think he’s a girl. He will ask me if I think this person is flirting with him and what should he say back.

I have never mastered the fine art of being a girl. I didn’t spend my teenaged years sitting around my pink bedroom with my friends talking about my period like the chick from “Are You There God, It’s Me Margaret.” I got sexually harassed and assaulted and consider it a miracle that I survived my teenaged years without committing suicide. I find it very difficult to get giddy and enthusiastic with this guy over things that caused me a great deal of shame and pain growing up.

Any time I try to make it clear to this guy that I don’t want to talk about make up and would rather go back to talking about Doctor Who like we used to, I get accused of being intolerant of his kinks even though he staunchly refuses to identify as trans.

I am trying to be tolerant. I think people have the right to do whatever they want to, but that includes me too who doesn’t want to spend days assuring a guy he looks pretty while he talks about how the underwire from his bra is digging into his chest.

I don’t know what to do. I don’t have anyone to talk to about this because he made me swear not to tell any of our friends he is doing this. I told a friend about it and she told me to keep it to myself because it would make me look bad to tell anyone that this guy is doing these things. I am incredibly depressed and upset and don’t know what to do.

Thanks.

Reluctant Girlfriend

DEAR RELUCTANT GIRLFRIEND: Whether your friend is trans or not is beside the point. The problem is that, cis, trans, non-binary or just kinky, your friend is kinda being an asshole. It’s one thing to be excited about something and really want to discuss it with a close friend. It’s another entirely to get pissy at someone you’re (general you, not you, RG) friends with and manipulate them into only talking about the things you want to talk about by insisting that they’re a bad person because maybe they’d like to talk about something else for once.

You’re right: the fact that your friend wants to talk about their crossplay or make-up doesn’t mean that you have to as well, especially if that’s something that makes you uncomfortable. Friendships go both ways; you’re allowed to have preferences too. Pulling the “you’re kink-shaming me” card is a manipulative and s

tty thing to do to someone when all they want to do is change the subject.

If this is them getting taking baby steps towards getting comfortable with their gender, then hey, more power to ‘em. It’s important to support your friends in times of crisis or confusion. But being a supportive friend doesn’t mean you don’t get to have boundaries, nor do they get to run roughshod over yours. This is a case where they’d do better to find someone who IS interested in talking about this. Not every friend in somebody’s social circle needs to share ALL of their interests or talk about ALL of them at all times.

So what do you do? Well, if your friend refuses to acknowledge your stated preferences and discomfort and tries to guilt you into playing along anyway… you break up with them. You can – and should – break up with friends, especially if they’re being s

tty to you. The fact that they may or may not be trans doesn’t give them a “get out of being an a

hole free” card, nor does their circumstances (whether their coming to terms with their gender identity or just discovering that they’ve got a specific fetish) mean that you’re handcuffed to them like you’re in The Defiant Ones. You’re allowed to stop being friends with someone for pretty much any reason, really. You’re not on the hook to manage their feelings or be their personal sounding board and cheerleading squad.

So let things end. It doesn’t have to be a big blow-up; you don’t have to make a production over dumping them as a friend. You can just as easily let things dwindle away – as friendships often do – by being less and less available if you prefer. But either way: give yourself permission to end the friendship. They can find someone who does want to opt-in and talk about make-up and boys and pretty dresses and you can find your fellow Whovians who want to come up with head canon about how Attack The Block is the time the Doctor met up with Finn from Star Wars and also how we really don’t need any more episodes about giant spiders, ever, thanks.

Good luck.

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