Ask Dr. NerdLove: How Do I Help My Single Friend?

I’m a big fan of your column and would like your insight on how to deal with a good friend of mine.

My friend, let’s call her Maude, is a wonderful friend: loyal, honest and kind. She is also incredibly introverted and rather socially awkward. It took me awhile to get to know her, but it was worth it.

Here’s the problem: despite being all things wonderful in a person, she really struggles in the romance department. I cannot stress how different she is as “good friend” versus “person seeking a boyfriend”. Although she is 30yrs old, I don’t believe she’s ever had a real boyfriend or serious relationship. As I learned from you, this is no big deal. The big deal that I don’t know quite how to address with her, is that she has behaviours that I can only describe as female incel. These are the entire reason she can’t seem to find a relationship.

Before I got to know Maude, I knew her mostly by reputation. A number of my guy friends had reported that she was a “stalker”. She will show up at places where she knows the object of her affection will be or at his place of employment and send dozens and dozens of texts asking for “closure” after casual sex or even mild flirtation with no physical contact. At first, I thought this gossip was just men being full of themselves or exaggerating her behaviour. It turns out that her reputation was well earned.

After a very long streak of abstinence after her “promiscuous phase” (her words, not mine), Maude decided she was ready to start dating again. Around the same time, a friend of mine had recently gotten out of a relationship. He’s good looking, smart and fun – however, he’s doing some post serious relationship tom catting around. In other words, he would be very fun to sleep with provided you did so with no expectation of a relationship. Surprisingly, Maude started hitting it off with him and really came out of her shell and they had some good conversations and went on one date several months ago. It ended in a hug. Since then, they’ve been sending flirty texts to each other in a kind of build up to a maybe sexual situation. Both of them confide in me, so without betraying each other’s confidences, I can say for certain he did have a genuine affection for her, but not as strong as hers for him.

Then the stalking and obsession started to kick in. He seemed to take it in stride, but he also is probably blissfully unaware of the behind the scenes work this woman does to get her man. She was getting irrationally upset and telling us girls about all these frustrations in this not even a relationship. This escalates over a few months and he naturally backs away as he’s been openly keeping time with a number of ladies. Finally, after a week of constant texts from her asking if she was being “crazy” for this and that and “should she send him another text” type bullshit, she went against all the ladies advice and sent him a missive about how she was very upset with him for “leading her on”. She was not led on. He handled it graciously, but backed off both the friendship and flirting. Since that fateful text, she’s been spiralling. All her social media posts are rather vague attempts to get his attention and she’s making a big deal about the few random dates she’s been on in an effort to make “him” jealous. In concert with her very awkward and public attempts to “date”, she has also gotten progressively militant about there being no available guys and making blanket statements about how men are only interested in looks etc. Long story long, she’s making herself miserable and inadvertently scaring away any man who might be interested in getting to know her. Also, her stalker reputation lingers, so that coupled with her introvertedness and bizarre takes on how relationships work is putting her in a pretty bad place.

I’d like to be understanding and want her to be happy, but her overall perception and approach to things are so far removed from my take on things that I don’t know how to remain supportive and provide useful feedback in a sensitive way. One can’t just say “well, you gotta stop this stalking and making up relationships in your head”. Should I just tell her to write you or do you have any ideas on how to gently wrangle her into healthier and more productive approaches to dating and sex?

Thanks in advance for any help you can provide here.

Friends In Need

One of the hardest things to do – and I say this as someone whose career is based around helping people date better – is getting people to recognize that they are their own worst enemies. A lot of this comes from the fact that people as a whole are very bad at understanding ourselves. We all like to believe that we’re far more self-aware and far more logical than we actually are. Men especially are fond of insisting on just how logical and rational and reasoned they are, never realizing just how much of their logic and rationality are just backfill. We assume that we’ve come to our beliefs and behaviors through simple cause and effect, a dispassionate examination of the events that brought us to what we believe. In reality, these are excuses, after the fact rationalizations for positions we’ve taken on the basis of pure emotion. It’s part of why so many “arguments” like the 80/20 rule and “women won’t date me because of my height” fall apart if you look at it for longer than a second; it’s an attempt to justify beliefs by pretending they’re rules akin to the law of gravity.

That’s why so often you’ll see people who are sabotaging their own success through asinine behaviors. They think the issue isn’t that they’re doing something wrong, it’s that they aren’t doing X, Y or Z HARD ENOUGH. In fact, you’ll see this fairly frequently in self-help circles or in organizations like Alcohol Anonymous… or groups like various Red Pill advocates, for that matter. The system doesn’t fail, you fail the system.

Even some of the people who write to me or who hire me for coaching are often less looking for advice, but rather for confirmation that it’s the world that’s wrong and they shouldn’t do anything different.

The problem is that until someone is willing to question those beliefs and admit that maybe they’re wrong, they won’t actually change. And we have a lot of psychological defenses that are in place specifically to keep us from changing our beliefs.

Case in point: Maude doesn’t seem to recognize that her behavior is driving people away. To her, it’s part of how she shows interest and affection. To everyone else… well, the most charitable description is that she’s acting like a character from a bad romantic comedy. And the fact that “this is just how I show my interest in someone” doesn’t make it excusable. “Just be yourself” may be the most common dating advice in the world, but it doesn’t work when “yourself” sucks and scares folks off.

And unfortunately, there is no way to wrangle someone into better patterns of thought or behavior until they’re ready for it. As much as I have issues with groups like Alcoholics Anonymous, they do get one thing right: nobody’s going to change until they believe they have to change.

So if you genuinely want to help Maude, the key is ultimately going to be to encourage her to start examining her own behavior. The tricky part is getting her to accept your advice. If you just go to her and say “here’s what you’re doing wrong”, she’s going to put her guard up and get defensive. She’ll almost certainly insist that you’re misunderstanding things or that there was context that you’re missing. Even if you were to go to her and say “Here is a list of all the things you’re doing wrong, backed by affidavits of eye-witnesses and the people you’ve attempted to date and also video evidence with slow-mo replay,” she’ll find any number of reasons why none of this “counted”. That’s why, at the end of the day, it has to feel like it’s her idea.

The way you do that? Is make her ask for it. Those moments when she says “what am I doing wrong” or “am I being crazy?” Those are the moments when you reply “Look, do you want me to give you a real answer?” She’ll almost certainly say “yes.” You’ll have to say “No, I mean, do you want me to give you a real answer, with the understanding that you may not like it?” If she says yes again – and she probably will – then you can start to break it down for her. By making her ask several times, you’re making her more invested in the outcome; she’s less likely to dismiss it out of hand. She won’t necessarily accept it, not right at first. But my making her work for it – asking for it multiple times – you’re increasing the likelihood that she’ll take it seriously.

The key is not to expect any one conversation to change her mind or make her decide to act differently. What you’re ultimately doing is planting the seed that will hopefully find purchase in her consciousness and cause her to question things. It may take time; she may have to repeat the pattern again and again before it really sinks in. But hopefully, that little bit of investment in the answer will start to cause her to reconsider. If and when she does, then she’ll start being ready to examine her own behavior and make a change. That’s the point where she’ll be more receptive to ideas about what she needs to do differently.

The other thing to keep in mind: you need to have your own boundaries too. Sometimes the most supportive thing to do is to refuse to engage, especially if what she’s asking for is for your tacit approval. For some people, part of what they get out of these patterns is the drama. They get to be at the center of this grand story that makes then the focus of everyone’s attention. There’s often a perverse part of them that likes it when things go wrong because they get to play The Wronged Party and get everyone’s sympathy and attention. And if that’s the case? Then the only willing move is not to play.

If the only thing she’s willing to accept from you is advice that enables her to keep going as she is, then you’re going to have to stand firm. You’re going to have to say “look, I told you what I think. You can accept it or not, but I’m not going to keep talking about this with you.” She won’t like that. In fact, she may go off on tirades about how you’re being a bad friend and a REAL friend would do this, that or the other thing. Stand your ground. It may suck, and you may find yourself at the center of an emotional shitstorm… but it will pass. You don’t need to be part of her performance.

And – as with making her ask for your advice – cutting off that source of satisfaction may be what helps motivate her to do things differently.

Good luck.

Hi Dr. NerdLove

I just turned 18 and I’ve never had a girlfriend, never kissed, you get the story. I’m sure you’ve seen this before, but I’m in kind of a unique situation and I’m not sure where to go.

I went to a high school that was not quite as social as most, and even there I was extremely introverted and nerdy. As a result, I have absolutely zero social experience, especially when it comes to dating. (I have some friends, both guys and girls.) I’m going to college in the fall and I’m worried that I’ll come off as really creepy (or I’ll freak out and never be able to flirt with anyone).

To complicate things further, I’m not really sure what I want. I used to think that there’d be plenty of time later to worry about dating, but I’m not so sure anymore. And I don’t really want to have casual sex, but that’s all guys seem to want in college. Apparently I’m already late to the game, and I don’t want to start trying to date (or worse, have casual sex) at 25 just to have every girl reject me for still being a virgin. I know it shouldn’t matter, but as far as I can tell online, very few girls would ever want to date older virgins.

What do I do? Should I start looking for any relationship just to get my first out of the way? How do I practice flirting and asking girls out for when I meet someone I really like?

Thanks in advance,
Sexually and Romantically Confused

You’re coming at this from the wrong angle, SRC. You’re assuming that you should have X amount of experience under your belt by now and know exactly what it is that you want. Except… that’s not how this all works. I realize that it feels like you’re running out of time. I realize it feels like you’re supposed to have figured all this shit out by now and be ready to attack the world with the sort of certainty that you only see in diehard Star Wars fans. In reality: you are incredibly young. It’s fine that you don’t know what you want yet because you’re just starting your life. You are still figuring out who you are and and how very goddamn big the world around you is. Even if you knew, with 100% certainty, that you wanted a straight-path to marriage – or serial monogamy or even just time to be absurdly promiscuous – you would start realizing that hey, maybe you don’t actually want this. Because I am here from the future to tell you: you will find that what you want from relationships is going to change all the goddamn time. You very well may have a monogamous period and then realize that you’re not someone who can do monogamy. You may spend time trying to be a player only to realize that what you want is to find Ms. Right and have a long-term commitment. You may be in a committed relationship and realize that you want that relationship… but not with the person you have it with.

And that’s all fine.

You’re in a period when you should be learning about who you are and trying new and different things. Going into dating with an attitude of “I’m not sure where this is going, but I’m interested in finding out” is just fine. You don’t need to have any kind of relationship that you don’t actually want, regardless of what it seems like everyone else is doing. Even if it seems like everyone is just fucking and nobody is dating (trust me: they aren’t and they are) you’re free to blaze your own damn path; you’re not obligated to anyone else’s idea of how you should date.

What you shouldn’t do is date someone just to date them. If I can give you some advice that will make your love life much happier: adopt a “fuck yes or fuck no” mentality. Don’t date someone just because you feel like you are supposed to. If you’re not excited by them, if you don’t want them to be a major part of your life? Then don’t commit to a serious relationship. Now don’t get me wrong: this doesn’t mean that you should only date people if there’re fireworks right from the start. Some relationships are a slow burn. It’s fine to date someone casually, without an expectation of commitment or it being long-term, if you feel good about them and want to see if things will develop. But dating someone just for experience points? That’s a shitty thing to do – to them and to yourself.

And as for the rest? You’re overthinking things … and getting some really bad advice in the process. Stop looking at Reddit or whatever other forums you’re going to for ideas about what All Women Want; while some women won’t want to date virgins, there’re more who won’t care or are totally cool with it. Hell, there’re some for whom that is their precise fetish. If you can make friends, you can find dates. The skillset is the same; the only difference is the end goal. Now I’ll point out that I’ve wrote my book New Game +: The Geek’s Guide to Love, Sex and Dating, speciofically for guys like you, and you should definitely check it out. But – and I realize this seems contradictory – that shouldn’t be your primary focus. What you should focus on doing over the summer – and even during your first year at college – is to practice being social. That’s it. Get used to talking to people and having casual conversations. We call them social skills for a reason; they’re skills and you can improve any skill with practice.

Trust me: this isn’t nearly as complicated or difficult as you think. Just focus on getting to know people and getting used to being social. Everything else will come with time and practice.

You’ll be fine. I promise.

Good luck.

This post was previously published on and is republished here with permission from the author.


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