DEAR DR. NERDLOVE: I have a friend who’s overly endowed in the penis area. He somehow makes this fact known in every situation that he seems to be in, which is his prerogative, but when it encroaches on myself and my own actions, it drives me crazy and in the past has led to a potential love interest getting redirected in his direction. 

He claims it’s not his fault, but I believe that he uses his endowment as a legit reason to push himself into the middle of everything. He seems to think he’s more important than anybody else because of his gift. I find this to be complete bulls—t personally. But the way that society works these days, people always gravitate towards whatever seems to be bigger and better. 

I know that that us advice you’re probably going to give is just to say stop being friends with this person and move on. And if it truly is that simple, that’s exactly what I will do. At the same time, I feel like I’m the best friend he has ever had and I might feel like a jerk for just abandoning him. But as a wingman I still feel like it’s unfair when he touts his attributes seemingly from the rooftops all the time, when he could handle it differently and incorporate me into the whole scheme, you know, up talk me a little bit to people and give me some props. But I never get any goddamn props, I always get leftovers. Makes me want to put my fist through a wall to be honest.

He’s The (Brat)Wurst

DEAR HE’S THE (BRAT)WURST: OK, once again I will reiterate my standard policy on fake letters: I generally catch the obvious fakes, but I’m not terribly fussed when someone manages to sneak one by me. Most letters are theoretical (and thus, functionally not real) to everyone but the letter writer as it is, but if there’s a lesson that other folks can take away from a potential fake, I find that value to be greater than the supposed “gotcha” of someone managing to slip one by.

Case in point: this letter. A lot of people have had experiences dealing with That One Friend and/or penis anxiety in general, so we’ll roll with it for a moment.

Let’s take the ongoing chorus of “Enormous Penis” out of the equation here and focus on this guy’s actual behavior. The long and short of it is very simple: whether he’s got a huge willy or not, he’s acting like a massive tool. It’s the cliche of “God give me the confidence of a mediocre white man” writ large, where he’s decided to make himself the center of attention at all times, regardless of the people around him or without consideration for either his supposed goals (being a good bro and wingman) or whether folks want to hear about his theoretically ginormous schwanz.

This is one of the times when we run into the difference between being confident and being an arrogant, pushy asshat. Someone who’s confident doesn’t feel the need to brag, boast or otherwise try to direct attention to his moneymaker. It’s not that confidence is always quiet and assured, but there’s not really a need to brag when you know what you’ve got, you know what you’re worth, and you know what you’re capable of. As a general rule, the louder that someone proclaims their vaunted superiority in some area, especially when it’s not relevant, the less secure they are about it… or in other areas, where they’re (ahem) overcompensating. It’s often about a need for attention and – importantly – validation. If it’s not about the thing they’re bragging about, it’s often an attempt to draw attention away from other inadequacies. Big d--k energy, as it were, is usually displayed as unwavering confidence other areas, not in loud braggadocio.

It’s not as though that confident and secure people can’t be loud and obnoxious, but much of it really comes down to “put-up-or-shut-up” time. LeBron or Jordan may be masters of trash-talk, but it’s talk that they can back up and do so, regularly. They’re among the GOATs precisely because they have the skills that make them the elite among the elite. The trash talk is baked into the competition, a challenge of skill – the declaration that “if you come at the king you better not miss.” Just rolling up on people with “what up I got a big d--k” isn’t the same, certainly not unless he’s in a literal d--k-measuring contest.

(Now, I will give some credit here: sometimes it’s just severely misplaced confidence. A lot of guys who legitimately have large penises tend to think of themselves as God’s gift to women. Most of them tend to be lousy in bed, in no small part because they’ve convinced themselves that size is the only thing they need to bring to the table. So foreplay becomes something that happens to other people, the g-spot is where they hang out listening to Snoop Dog and the clitoris is a piece of equipment they’ve never seen but they’re pretty sure isn’t necessary anyway and they miss the bored and pained expression on their partners’ faces while they jackhammer away.  Meanwhile, 70-90% of women can’t orgasm through penetration, so Johnny WangDoodle ain’t got the stroke game he thinks.)

The bigger issue however, is that he’s a boor, a bore and a snore. Rolling into conversations with “oh, have I mentioned that every time I get an erection I nearly pass out because it needs all the blood in my body” has all the charm, poise and believability of Danny DeVito pointedly “accidentally” dropping a Magnum condom. For the folks around him it’s about as welcome as morning wood while trying to pee or something sus prodding your lower back on a crowded subway. And that’s before we get into the fact that he’s neither a good friend nor a good wingman. A wingman’s entire job is to support his or her friend. That means helping clear a path, handle logistics, provide moral and emotional support and be the Flavor Flav to their buddy’s Chuck D. This is something that is supposed to go both ways; you support and prop them up, they do the same for you. If all this guy is doing is dominating conversations in unwelcome ways, turning the topic to him and otherwise blowing up a promising connection, then he’s not being a wingman. At best, he’s a grenade with the pin about to fall out at any moment. At worst, he’s a poacher. And none of it makes for being a good friend.

Now all this having been said: this isn’t about the world “gravitating to the bigger and better”. Trust me, the only people who care that much about penis size are straight cis men. This isn’t about the world catering to him, it’s about this guy being loud and obnoxious and getting all the attention… even though most of the attention is “who the hell is this freak and why is he going on about his wang?”

This is an area where, if you think it would be worth it, you should have a very long, and firm conversation about his behavior, how it bothers other people and how it affects you. Because, as with most cases, it’s not that he “can’t help it”. If he’s not acting like the big swinging d--k to, say, his boss, his teachers or the cops? He absolutely can. He’s doing it with you because you let him get away with it. Once he gets his d--k knocked into the dirt, I suspect that that tune would change.

But if he doesn’t want to listen (presumably because the blood rushed away from his brain after thinking about Sydney Sweeney in a micro-bikini), then the best thing you can do is get a better class of friends. You may be the best friend he’s ever had, but he’s decidedly not returning the favor. He’s being an absolute knob to you and the people around you. That’s on him, and you don’t have any obligation to hang around just because you’re the only one who tolerates him. If he doesn’t want to alienate people and drive friends away, he can stop acting like a bellend.

So have a word with this friend-who-definitely-exists and if he doesn’t or won’t listen? He can go spend his time with his buddies John Thomas and the twins and be with people who might actually appreciate his schlock. Or his schlong.

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

DEAR DR. NERDLOVE: Last year summer of 2023, I ended my engagement with a man I was with for five years. He lost his job, fell into a major depression which led to substance abuse, which resulted in sex addictions like messaging hookers.

Unfortunately, this was not my first rodeo with his behavior like that. I had dealt with other betrayals before and his inappropriate behavior towards other women. In 2021 we broke up for a few months because he tried cheating on me with our roommate.

I had thought he had his “coming to Jesus” moment after 2021 so I stayed. We went to therapy and he promised and said everything I needed to hear. We had a beautiful year and a half together. This is a man I’ve loved since middle school, always had a crush on him, and was head over heels when I finally got a chance to be with him.

Ever since our relationship ended, he has been telling me he wanted to be with me and make things right.

In May I decided to give us a chance. We would get in quite a few heated arguments but I was invested in making it work and give us a chance at repair. One argument we had a lot was about a new friend of his we will call Jackie. Jackie was coming over a lot and when she sent him a middle of the night message when he was staying at my house, I got red flags.

Anyways, fast forward to this month and I find out while I was trying to repair our relationship, he had hooked up with Jackie. He tells me that him and I weren’t officially together so it shouldn’t matter. He tells me I’m being psycho and irrational and unreasonable.

I definitely have not made our repair easy. I’ve escalated fights and said harsh things. As of now our relationship is completely over and I’m telling him we are broken with no chance at repair. Am I overreacting? Should I not care if he was hooking up with another girl if him and I weren’t officially back together yet? Obviously his lies and gaslighting were problematic. But I’m considering what he did as betrayal. Am I wrong?

Thanks.

Always Betrayed

DEAR ALWAYS BETRAYED: So I’m going to apologize in advance for a tangent, but you accidentally hit a “push button, get rant” trigger of mine: unless you left something out, it doesn’t sound like he was gaslighting you. Gaslighting is one of those terms that people have started misusing; it doesn’t mean lying or disagreeing about how to interpret something, it’s when someone is deliberately trying to make it impossible for you to trust your own judgement and senses. There’s a difference between saying “I’m not seeing anyone else” when they absolutely are and “You didn’t see me kissing Jessica, you’re crazy.” 

(Or to put it another way, the more someone’s behavior resembles the song “It Wasn’t Me”, the more it’s akin to gaslighting.)

OK, anyway.

In all sincerity, I really don’t think “is it unreasonable to be upset about this” is a question that needed to be asked. While I firmly believe that you shouldn’t assume exclusivity until you’ve had the “are we exclusive” conversation, there’s a distinct difference when someone who cheated is trying to prove you can trust him again. I understand why you would want to give this guy the benefit of the doubt and why you wouldn’t want to think that he’s the kind of guy who could be this s--tty to you. You’ve carried a torch for him for a long time, and it’s hard to think of someone you’ve had feelings for being this much of a d--kbag. But that’s what he’s doing, and he’s doing it in a way where he knows he’s being s--tty, but he doesn’t want to face the consequences for doing so.

This is  a situation where someone is technically correct, but even being technically correct doesn’t mean that he’s not also being an absolute s--thead.

Yes, technically you and he weren’t back together, and so technically there wasn’t an expectation of commitment or exclusivity. That much is correct, as far as that goes.

However! 

The fact is that you were working on fixing the relationship with him in good faith, with an eye towards getting back together. He, likewise, said over and over again that he wanted to make things right, went to couple’s counseling, said all the right words and so on. While he didn’t say or make any promises regarding exclusivity or monogamy, I think most reasonable people would assume that someone making all of those promises and appearing to actually be putting in effort is not also pursuing other people unless otherwise specified. 

(Polyamory and ethical non-monogamy are examples of when this would be less reasonable, but seeing as you were in a closed relationship, it doesn’t apply here.) 

So I don’t think it was unreasonable to assume that there was an implied promise of exclusivity, or at the very least, making a point of not dating or putting other dates on hold, especially in light of the fact that you broke up with him before when he tried to bang your roommate. Violating the commitment he made is part of what ended the relationship in the first place. Since he violated your trust before, if he wants to get back together with you, it makes sense to assume that he would want to re-earn your trust by proving himself to be trustworthy.

The fact that he was f--king around with Jackie while doing this belies the intent and sincerity of his actions. If he meant it, then he has a weird way of showing it. If he didn’t mean it, then he’s just being an asshole and playing you for a sucker. 

The fact that he also tried to pull a “well technically we’re not together” over this should really tell you everything you need to know.  He proved time and time again that he’s so full of s--t that his eyes turned brown. I get that you’ve had a thing for him for a long time, but he’s already hurt you at least twice through his choices and actions, and he’s proven that either he doesn’t mean what he says, or doesn’t know himself well enough to not make promises he can’t keep. Both are exemplary reasons to never date him again. This revelation (and his subsequent “you’re not allowed to be mad at me because reasons”) puts him into pure “curse your sudden but inevitable betrayal” territory.

So no, I don’t think you’re wrong to feel hurt by this nor do I feel it’s unreasonable for you to be upset by it. I think it’s entirely fair to see this as a betrayal. He told you, repeatedly, that he wants to be with you and make things right while he goes out and bangs another person. Well, as I’m always saying: deeds, not words. His words say one thing, his deeds say another, and what they say is “drop kick this dude to the corner with the rest of the compost”.

So TL;DR: he may be technically correct, but that doesn’t mean that he’s RIGHT. Someone who’s going to try to lawyer his way out of consequences despite those actions going against the spirit of what he promised is someone who you are well rid of. Consign this guy to the Dumpster of Bad Dates Past and don’t let him take up any more of your bandwidth. And the next time someone says one thing but his actions indicate the opposite? Trust the deeds more than the words.

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

DEAR DR. NERDLOVE: I recently found your page and I have read a bunch of your posts and I think you have generally good advice but one thing I haven’t been able to find much of is about the talking phase because I am new to it and I don’t know how to navigate it very well.

Basically, I am a 18 year old male who just started college and until this point I never went out of my way to talk to girls. I am a decently attractive dude I think and I have had a number of people have crushes on my throughout my life but I never really wanted to go anywhere with them. Now that I have gotten to college I wanted to try and push myself out of my comfort zone and start looking to talk to girls, which I had been very nervous about until recently, where I finally got the courage and it really isn’t as hard as I thought it would be.

Last week I went up to a girl and we started talking and I got her number, we started texting and we continued texting for about 3-4 days before she started losing interest and then things didn’t really go anywhere from there and we haven’t texted since. There was another girl last week that I found really attractive so I walked with her after class for a while we were really vibing I felt like and I got her number but she responded once and then didn’t respond again. Then like 3 days ago I was outside and I saw a really good looking girl who was staring at me off and on for 30-45 minutes and smiling as I walked by, so I feel like she must have thought I was attractive. She was with a friend who was on the phone so didn’t want to go up to her since I didn’t want to interrupt her friend, but I did mouth asking for her number from another bench, she got up excitedly and gave me her number and we started texting basically the rest of the night but I could feel her losing interest as the night went on, but she did said goodnight so I thought that was a good sign. Then the next day comes around and she messages me in the morning and then doesn’t until 10 PM where I then ask if she wants to hang out a bit the next day and she says that she wants to focus on school and stuff. Now about 2 days ago, I remembered this girl from one of my classes and I thought I should try and message her since I got her Instagram and I tried to be more fun in the messages and I could see a massive difference with how they responded and stuff, towards the end of last night I asked if I could get her number and she said she wasn’t looking for something right now and wanted to focus on school but she still wants to be my friend. I said that I would because I genuinely did enjoy our conversation.

Now this is all in the matter of 1 week so not a very big sample size but I can’t help but feel like I am doing something to lose interest. I am not sending anything weird at all over text, I am just asking questions, and occasionally complimenting them with which they respond “aww thanks,” which I think is where I am messing up but I want your thoughts. I have been asking general questions that don’t take much thought and they answer with short messages, and I think that’s where I am messing up, they take on average about 3-4 hours to respond. Of course, I know that I need to be more fun like I did with the last girl, by joking around, and being more myself, and she did seem more quick to respond sometimes right away, but that ended up with being friend zoned. But I was also thinking that maybe I should try calling them sometimes, I saw people online say calling is generally more effective so I was wondering if next time I should try that, and if I should, how should I go about it?

Also this is a side question I wasn’t sure the answer to and I couldn’t find anything online about, I was wondering if there is like a limit on how much I go up to women, like if I see a girl I think is attractive should I go up to them even if I have talked to one earlier, or should I try and not go up to too many, I ask because I don’t want to be seen as down bad going up to a ton of girls lmao, but I also want to try and shoot my shot if I think a girl is cute because the other ones might not work out.

Take The Shot

DEAR TAKE THE SHOT: Congratulations on taking steps and getting the courage to be more social and working on meeting new people, TTS!

Now, the first thing I will tell you is that this is something of a skill issue. That is, you’ve never really done this before, and so you’re still figuring things out. It’s a little like using learning any skill for the first time; you’re going to stumble, make progress, stumble again, make progress, completely mess up, stumble, mess up, make more progress. This isn’t a marker at being undesirable or being uniquely unskilled, it’s just how everyone learns. Even people who are naturally gifted have to practice and develop their skills. This is why we call them social skills. So I wouldn’t stress about it too much and instead focus on trying to see what you could do differently or better with each interaction and what you could learn from them.

Now that having been said, I don’t think the issue is anything in the messages per se. I think the biggest problem, such as it is, is that you’re taking a shotgun approach to meeting women and this is the inevitable result.

One of the things I always tell folks is that meeting someone is often a matter of right place, right person, right time. If those things don’t line up, very little is going to happen, and you can’t control for all three. It is, however, a lot easier to adjust those odds when you take a more targeted approach at finding people who are right for you. You’re much more likely to find someone who’s going to be compatible with you if you meet them at an event based around something you both enjoy. Similarly, meeting people in social venues means they’re more likely to be in the mood to be social and talk with a charming stranger. And of course, in spaces that are explicitly for people interested in dating – speed-dating events, dedicated MeetUps, dating apps, etc. – you’re meeting people who are open to dating. 

When you take a scattershot approach like you have, you’re going to run into a lot of people who are in relationships (wrong time), who are focused on other priorities (ditto), who don’t want to talk or don’t have the time (wrong place), or who may well think you’re nice enough but simply don’t want to date you (wrong person). In those cases, there’s really nothing that can be done. It’s not that you’re not whatever-enough, or that you should’ve called instead of texting,  it’s that those are people who aren’t going to be interested in dating for any multitude of reasons. The only thing you can really do is shrug your shoulders and move on with the understanding that this is part and parcel of the shotgun approach.

The next thing I would point out is that you’re moving very fast in terms of trying to turn these into dates, in a way that’s not that conducive to your goals. This style of cold approach – basically, approaching random people in non-social, non-dating spaces  – is very inefficient in terms of actually getting dates overall. I recall one would-be pickup artist who documented his street approaches and came to the realization that, over the course of three years, he had an approach-to-date success ratio of 1%. If you factored in dates that lead to sex, his success ratio dropped to fractions of a percentage point.

The challenge here is that you’re essentially trying to convince a total stranger to be interested in starting a potentially romantic or sexual relationship with you after knowing you for less than an hour – even factoring the texting. That’s not varsity level difficulty, that’s damn near Olympic level difficulty.

The fact that you’re getting numbers and texting is good, and you should be proud of yourself.  However, it’s going to be very hard to turn most of these into dates. And the single biggest reason is that you really have next to no connection with any of them. From what you’ve described in your letter, these are all ice cold approaches, with people you’ve only really interacted with for what seems to be minutes at a time. There’s just not that much of a foundation to build on that you could turn into enough attraction that they’d want to go on a date. Even on dating apps, you’re usually talking for longer and you’ve got the benefit of your mutual profiles to check for signs of compatibility. As it is: you know next to nothing about these women and they know next to nothing about you. You’d have to be building rapport and finding commonalities very quickly and be pretty skilled at using those to build a sense of attraction between you two to make this work the way you’re trying.

Now, in other circumstances, I would say that part of the issue is not inviting them out on a date. But seeing as these are people you’ve literally just met and have only known for the length of time that you’ve been texting, I’d say that instead, you may want to commit to getting to know them better and chat, rather than angling for a date. Remember, you know very little about them other than you find them physically attractive, and they know just about as much about you. Getting to know them makes it a lot easier to find out if there’s enough there that would make it worth your time to date them; after all, our time on this earth is limited and you want to spend as little as necessary on folks who just aren’t right for you.

I think it would also be helpful to see this as practice in getting used to just connecting with women and making friends rather than being laser-focused on dates and relationships. The women who are focused on their studies or who are in relationships with someone else can still be great friends – possibly even people who might introduce you to their friends once they like and trust you. But that means being willing to genuinely be their friend, not hoping to find an angle to parlay that connection into a relationship via the Nice Guy Back Door Gambit.

Another thing that will help, especially since these are women you’ve literally just met, is inviting them to group events rather than one-on-one dates. Organizing, say, a cookout if your local park has grills for folks to use, a karaoke night or a NERF war on the quad or other events for you and your friends gives you a low-stakes, low-pressure event to invite these women to that doesn’t feel like a date with a stranger. It’s a lot easier to say yes to “hey, I’m hosting $ACTIVITY with my friends this weekend, I think you’d dig it. You should come by if you’re free. Feel free to bring friends!” than committing to being with someone you don’t know for an hour or more. This gives you a greater opportunity to talk with them, for them to see you in your element and generally for you to help everyone have a good time – something which triggers the Reward Theory of Attraction and helps encourage them to want to spend more time with you. The more they like hanging out with you – in groups and solo – the more likely they are to be interested in dating.

As for your last question: there’s no real limit outside of time and ability to maintain multiple connections or conversations at once. You do run the risk of getting a reputation depending on when and where you’re doing all these cold approaches, however, especially if its consistently in non-traditionally social spaces, though how much of an issue that can be depends on a lot of factors.

However, like I said: this is a very inefficient way of meeting women and dating them. You’d do better to date slow – that is, get to know folks over time, rather than shotgunning your attention all over the place. It’s a lot easier when you focus on meeting the people who you are most likely to be compatible with, rather than throwing lead in the air and hoping you get lucky.

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