How Do I Finally Break Out of My Shell Around Women?

Hi Dr. NerdLove,

I’ve stumbled across this site about a year ago and have really been reading and trying to take your advice in all kinds of areas of my life. I have always been fearful of showing my vulnerability to people and it even lead to issues with some of my ex-girlfriends. I have for the past few years been improving on and genuinely showing myself off to people. The reason I did this was because I tend to have a lot of people who end up letting their guard down with me very easily and telling me about their mental health struggles such as depression, suicidal thoughts or attempts, cutting themselves, abuse, etc and they find I’m a very easy and caring person to talk to about this. I didn’t want to feel like burdening people who may have those issues with problems going on in my own life that felt minuscule in comparison, so I hid it. It was unhealthy I admit, but I was doing it for what I thought was for the benefit of someone who was suffering in my eyes. These days although I am still someone who hears this kind of stuff, I have made it more of a mission to be more active in saying how I really feel when asked rather than always replying “I’m fine.”

My problem I still have yet to fully overcome, however, is really expressing attraction to people I actually would like to have sex with. Granted, women (and men) have told me that I am quite attractive and I have for years even had women chase after me to either become a boyfriend or do sexual activities with me, but I was always someone who was just passive with it all. I’ve had a total of 5 relationships so far and all of them were initiated by the women asking me out. I lost my virginity only a few months ago and it was due to me striking up a conversation with a women who sat by me in a bar and she slid over her number after the conversation to which I followed up on and had sex which she said I was an enjoyable partner. For reference, I am 23 now.

I keep thinking in the back of my mind that being too forward about maybe getting a Friends with Benefit situation or even a one-night stand  to be inappropriate (despite the fact I know women are also sexual beings). Thus, I feel like I have to always be super respectful in that category, which leads to me being really slow to initiate things sexually, even though I am confident in expressing interest in general attraction more generally although again in a passive manner.

So I want to ask, what can I do to become more confident in being active in my flirting and being comfortable just trying to get sexual relationships without much else attached? I don’t just want to keep being the passive guy who although can occasionally get females interested. I largely just never go after who I want due to my own insecurities about the man I’m trying to be.

Holding Back

First thing I’m always gonna tell folks when this comes up: do yourself a favor and don’t use “females” as a collective noun to refer to human women. At best, it’s awkward and vaguely dehumanizing; at worst, it leads folks to think you’re like the incels and RedPillers who deliberately call women “females” in order to mark them as lesser.

Plus, it makes you sound like a Ferengi. And not one of the quasi-loveable ones from the later seasons of Deep Space 9.

Now with that out of the way, let’s talk about problems and the underlying causes.

I don’t know if you’ve twigged to this already, HB, but there’s a common thread between your avoiding vulnerability and finding a friends-with-benefits relationship. You even touch on it in your letter: you feel like you don’t “deserve” to express yourself to other folks. The reasons vary — with the former, you don’t want to complain when their problems are worse, with the other you fear being inappropriate — but the outcomes are the same. In both cases, you’re working from a position that your desires or wants are unwelcome, inappropriate and would otherwise be a burden or imposition on others. This leads to your being incredibly passive and reticent, staying quiet even when others are actively telling you that they want to hear from you.

And the thing is, it’s not true. If you were to ask your friends, even the folks having serious problems, then you would almost certainly discover that they want to support you when you’re having problems. Think of how you would feel if you found out your friends were afraid to ask for help or support because they thought that their problems weren’t important or significant in comparison to what you’ve got going on. You would probably feel a little hurt or upset that they felt like they couldn’t come to you. Well, the same goes for your friends.

Now, the trick is that you want to pay attention to timing and read the room. You don’t necessarily want to interrupt someone who’s telling you that they just… I dunno, got fired and are about to get kicked out of their apartment, in order to tell them that that you’ve got a shitty coworker who keeps stealing your lunch out of the breakroom fridge. However, that doesn’t mean that friends don’t ever want to know if you’re having issues, especially if they’re genuinely asking how you’re doing. It just means that you want to give them your full attention and consideration while they’re sharing, same as you would want from them.

Many times, when folks are sharing their struggles, they’re both letting you in — here’s what they’re dealing with —  and venting. What they want more than anything else in that moment isn’t a solution, it’s just a friendly ear to listen and say “wow, that really sucks, I’m so sorry”. That doesn’t mean that your problems aren’t problems, nor are they less important; it just means in that moment they’re asking for something from you. That’s why the key is to avoid having the “well that’s a shame, NOW LET ME TELL YOU WHAT A REAL PROBLEM IS” one-upsmanship competition.

If someone asks about your problems after having unloaded those heavy moments, all you really need to say is “Well, I’ve got some stuff going on, but that can wait; how can I help you right now? Do you want to brainstorm a solution or do you want an ear and sympathy?”

(Incidentally, getting good at just listening without trying to solve people’s problems will go a long, long way with the women you want to date.)

The same underlying issue applies to your fear of expressing yourself openly with women you’re looking to sleep with. You worry that your interest in no-strings sex is inherently insulting or an imposition on others, despite there being folks who clearly are into you, and so you feel like you have to let other folks take the initiative. Unfortunately, this doesn’t work so well when most of the other folks you’re likely to encounter are going to feel equally as restrained in expressing their interest. Someone’s gotta put their cards on the table first, and it may as well be you.

However, it seems like you’re equating “respectful” with “not making a move at all”, rather than the incredibly low bar of “don’t be a pushy asshole“. I think part of the disconnect you’re having is that you’ve framed this dilemma to yourself as the dichotomy between “say nothing” and “point at crotch, make a ‘giving a blowjob’ face, waggle eyebrows and go ‘enh? enh?’” Expressing yourself sexually isn’t just about bluntly saying “nice boobs, wanna fuck” to someone at a bar, it’s about being open and honest about what you want. Flirting with someone you like, for example, is part of expressing yourself. It’s part of how we show interest in others, especially romantic or sexual interest. Showing that interest is important too, considering that women can be just as worried, anxious or nervous about whether folks are interested in them. 

Much as with “when’s the right time to share my problems,” the key is to read the room. Someone who doesn’t respond when you flirt, or who deflects any sexual flirting or tries to bring the topic to non-sexual  topics? That’s someone telling you they’re not interested or comfortable and they’d rather you stop. If you continue, then yes, you’re being disrespectful (to say the least). If you back off? That’s fine; you’re saying “ah, ok, you’re not interested, not a problem, I’ll stop.” Similarly, treating someone like they’re only their for your consumption? Disrespectful. Flirting and teasing and playing with someone who is clearly into it and is reciprocating? Not disrespectful.

Now, having the “here’s what I’m up for” talk — similar to the “Defining The Relationship Talk” — is another area where expressing yourself is important; it’s the way you go about things that’s crucial. Most folks aren’t likely to respond well to “hey, wanna be FWBs?”, especially if it comes out of the clear blue sky from a stranger. A better approach is to take a moment to say “Hey, I want to make sure we’re on the same page here; here’s what I’m looking for, here’s what I can offer, here’s what I am not up for,” and lay out exactly what you’re looking for. And when I say “exactly”, I mean just that. A lot of folks will use confusing language because they are worried that being direct will “ruin” things. The problem is, the desire to avoid ruining the moment or seeming too blunt actually causes more problems than it resolves. Telling someone “I’m not looking for anything serious,” can mean a whole lot of things. Telling someone “hey, right now, I’m not interested in commitment or exclusivity, and I don’t expect it from you,” on the other hand, is clear and straightforward. It opens the door to talk about what that would mean, what you are interested in and what they want. That is far more respectful of their feelings, their interest and their time then by just saying whatever and hoping that your “not serious” is the same as theirs.

It’s worth nothing that there are times when you’ll run into folks who aren’t used to that level of honesty and directness. Some folks will be put off by it because it’s unfamiliar. Others will be put off because they’ve had a lifetime of being taught that you just don’t talk about sex like that with someone. That’s fine; some people need to have someone else open that particular door before they realize they could walk through it. People who find that sort of respectful directness distasteful are showing that you and they aren’t right for one another.

Of course, there’re also folks who won’t listen and will hear whatever it is they want to hear, no matter how plainly or even bluntly you say it. I’ve been on both sides of that particular equation — both as the person who heard “I’m not open to being someone’s girlfriend” and thought “Well I bet I can change that” and the person as who said it to people who didn’t take me seriously. You can’t control for that; all you can do is just remind them that you told them what you were and that hasn’t changed. That, too, is a form of showing respect.

It’s also a way of expressing boundaries, which is a skill you will want to cultivate,  incidentally.

At the end of the day, there really isn’t some magic trick to becoming someone who’s more assertive and who goes for what they want. You have to just actually do it — including being comfortable with telling folks that you are only looking for a casual or no-strings relationship. Do, or do not, as the sage says.

Oh, and one more thing: these are conversations to have before the clothes come off. Yeah, you can get caught up in the moment, but the last thing you want is to find out you thought you were having a casual fling and they thought this was leading to something more serious. Get in the habit of checking in with folks before you have sex to make sure you’re both on the same page.

Good luck.

Hi, Doc! This isn’t a problem I have, but rather an answer to a guy who wrote you recently lamenting about his lack of dating life. He immediately described himself as a “beta” and then poured out his woes. So I wanted to tell him why I wouldn’t date him, and it’s not for the reason he thinks. It’s not his looks, his job, his love of video games, his social awkwardness. It’s because he used incel language and that language is going to make most women drop him like a hot potato that was just cooked in the center of the sun.

I think a lot of guys who aren’t true incels pick up incel language online. They pick up terms like alphas and betas or Chads and Stacys without realizing that those terms come from a hate community. Specifically a community that hates women and promotes violence against women. The incel community specifically promotes sexual violence against women. So the second a guy describes himself as a “beta” the first thing a lot of women are going to think is, “Oh, hell no, incel alert! This guy is going to try to rape me, kill me, and put my body parts in his freezer.” And they run in the other direction.

Now I know a lot of guys who might read that and be offended. They are thinking “I’m not like that! How can anyone think I would be like that?!? I’m a good guy!” But women can’t afford to take a chance. The best estimate anyone has is that a woman has a one in three chance of being raped in her lifetime – and that doesn’t count sexual assault and sexual harassment, stalking, etc. Men will say women don’t think logically, but in fact we can do a risk/benefit analysis, and no one wants to go on a date thinking, “Maybe this will work out really well. Or maybe he’ll roofie and rape me.”

If you aren’t really an incel, get the incel terms out of your vocabulary and I promise your dating life will improve amazingly. But in the meantime, if you use the “n” word, I’m going to assume you’re a racist and I’m out of here. If you try to twirl me around when we meet the first time, I’m going to call you out on your PUA moves and probably end the date then and there. And the only time you should be talking about alphas and betas is if we’re discussing Teen Wolf.

I plan to start dating again soon and although I’m considered pretty hot, I am not looking for that BS “six sixes” thing that you know was made up by a guy, not a woman. I’m going for the 3 S’s – smart, sweet, and sexual. The guy I want to date is more into video games than sports, and was probably in the chess club or science fiction club in high school, not on the football team. But if you call yourself a beta, you’ll never hear from me again.

Legend of the (3S)Seeker

Good point, L3SS! The only thing I would have to add is that it’s not always or even exclusively incel language. A lot of the whole “alpha male/beta male” schtick’s been in the mainstream for a while; Christopher Moore described the main character of A Dirty Job as a “beta male” back in the early 00s, and the whole “be more alpha” has been around in one form or another for longer. It started off in business pop-psych guides about dominance and authority and moved into the mainstream from there.

However, you’re absolutely correct: folks who unironically use that language are signaling that they’re probably not a good match for you and best to be avoided.

Thanks for sharing your insight!