Inside The Mind Of Guys Who Are Shy And Inexperienced With Women

Dating advice is outside the scope of this site, with this article being a semi-exception. Over the years several women have written me to tell me reading this site has helped them understand the actions of a shy guy they were pursuing. With that in mind I thought I'd try to be in even more helpful and write a whole article outlining what it's like to be a man who's really shy and inexperienced with women. At the end I give a few thoughts on what to do if there's a shy guy in your life you're interested in.

Combined, the points below will describe a guy who's really, really inhibited and awkward around women. Not all shy men will have issues that intense or have every characteristic apply to them. I'll list some quick suggestions at the end, but for the most part I'll describe the issues shy guys deal with and let you draw your own conclusions about how to act. As with all the other writing on this site, the points here are from a mix of my own experience and accounts I've come across of how shy guys say they think.

I also wrote a follow up to this article on some of the unique issues shy women struggle with.

They're really nervous around women

I'll break this down further below, but their central problem is that they're just really anxious, scared, and inhibited around women. Almost all men get somewhat nervous when they have to ask girl out, or kiss her, or even talk to her for the first time. But when a guy is really shy his nervousness is at a level where it usually prevents him from doing any of those things. It's legitimately strong, not something where they can just take a deep breath and push through it. Sometimes this nervousness shows up as the physical symptoms of anxiety. At other times it's more of a powerful, paralyzing hesitation. Like they know how they want to act, but an invisible force field is preventing them from doing so.

They're nervous about talking to women they're interested in

This could mean feeling too anxious to start a conversation with an attractive stranger they've just noticed at a party. It can also be longer term. Some shy guys, especially younger ones, have had a crush on someone for years and years, and have never worked up the nerve to talk to her. The occasional time that someone they fancy talks to them first they often get too flustered, and the resulting brief conversation consists of some stuttered half-coherent answers on their part.

That's not to say a shy guy won't sometimes be able to chat to someone he's into, but it's relatively rare. Sometimes they just won't get nervous around someone for whatever mysterious reason. At other time they can force themselves to do it, but they're a total wreck inside the whole time.

They can be able to "set them up", but not "knock them down"

One problem that can plague shyer guys is that sometimes their nervousness doesn't appear when they first meet a girl, but comes back to bite them soon after. Initially they manage to come off as calm and charming and make a good impression, but then fall apart when the stakes get higher. The reason this happens is that when they first run into that women she's new and they haven't had time to over think things and attach any nervous feelings to her yet. They'll come away from the interaction feeling excited and optimistic about where things may lead.

However now they have a reason to feel pressured and jittery around her, and that's exactly what happens. The scenario then goes in one of the following directions: They're too nervous to talk to her again; They do talk to her, but they're such a withdrawn, obvious wreck that she's not interested; They talk to her, but are too nervous to be themselves, end up acting like a goofball, and shoot themselves in the foot; They're so nervous that at that immediate moment escaping the anxious symptoms takes precedence over anything else, and they act rude or aloof towards her to purposely sabotage their chance.

This 'setting them up, but not following through' scenario can happen to different degrees. The first is when a guy simply sees a girl around a few times and makes confident eye contact with her. She seems attracted and intrigued and like she's waiting for the guy to approach her. He sees this, gets nervous, and never conjures up the guts to speak to her.

Another variation is when a guy runs into a girl, say because he sits beside her in a lecture, chats to her for a bit, and comes off well. She seems interested. Enter the pressure. He can't work up the nerve to talk to her another time. A third scenario might be something more drawn out, like a guy has a few conversations with a girl he never really thought of as more than someone friendly to talk to. He notices she seems like she's becoming attracted to him, and he blows things soon after.

They're nervous about asking a girl to hang out

Hanging out, going on a date, the idea is the same. Sometimes a guy will be able to talk to someone he's interested in, often because the circumstances put them together, so the onus wasn't on him to approach anyone. If they like someone they'll often feel too nervous to ask them out and face the awkwardness and risk of rejection that entails. They may never ask them out, or put it off so long that by the time they do they're well into the Friend Zone.

They're nervous about making a move

Even with all of the above stacked against them, a shyer, inexperienced guy will sometimes have enough things go their way that they end up in a position where they're alone with a woman and want to 'make a move' on them (e.g., kiss them, put their arm around them, etc.). Unsurprisingly, they're really nervous and hesitant about this as well. Same general discomfort and risk of rejection.

They may have a blatant, all-systems-go opportunity where the girl is clearly interested, but they can't manage to go through with it. There they are, sitting on a couch watching a movie with their date when the credits start to roll. She turns to face him, looking into his eyes expectantly. He returns her gaze and pauses for a moment, and a little longer, and a bit longer still... then he gets up and asks her if he can get her anything to drink. Afterwards he's kicking himself for being so spineless. He was trying to work up the nerve to kiss her all evening, and kept wondering if now was the right time to do it, but in the end he couldn't pull the trigger.

One key fear guys have in this situation is if they're sexually inexperienced they're worried their embarrassing secret will be outed, and they'll be humiliated. They may think something like, "I've never kissed a girl. I don't know what I'm doing. What if she can tell I've never done this before?" Naturally they feel caught in a crappy Catch-22 where they need some experience to feel confident making a move, but they can't feel confident making a move until they have some experience.

They're intimidated by girls who they perceive as more being experienced than them

And when you're really inexperienced yourself it seems that's pretty much every woman. Part of this comes from a belief that no girl would be interested in a shy guy if she's had already had a few boyfriends. It also goes back to that point I mentioned in the last paragraph about them fearing their inexperience being outed.

This hinders a shy guy in two ways. First, they'll often rule out more obviously experienced girls as prospects. Too scary. Only harmless, innocent-seeming girls don't arouse their fears. But there are only so many women out there who are just as shy, innocent, and inexperienced as them, so it really cuts down their possibilities, and makes them put that much more pressure on themselves when they do find one who fits the description.

Secondly, if they're into a girl, and she seems into them, and she says something that draws attention to her comparatively higher level of experience (e.g., mentioning an ex-boyfriend), they'll get dejected and give up on her. She seems a lot more daunting now. And they figure, why would she want him? She has experience, he doesn't. It's never work out.


With time many anxious guys can slowly face their fears and gain enough experience with the opposite sex that they're not as held back by their anxiety as they used to be. They can start dating like everyone else. However, they may always have a tougher time of it than some men. They're often late bloomers, since their nerves and general social awkwardness kept them from getting into the game as early as everyone else.



They're insecure and hard on themselves about dating

When a guy is shy and not confident about women insecure thoughts often flow through their heads in an effortless stream; "I'm hopeless. I'll never get better. I suck with women. I'm a loser. I'm not good looking enough. There's no way that girl at work actually likes me. I totally screwed up with her the other day when I made that dumb joke. I give up."

It's all quite self-sabotaging. First, a lack of confidence isn't all that attractive. Next, they can be hyper-alert for any signs of rejection, and almost eager to conclude the worst. For example, if they're casually chatting to a girl and she mentions a TV show that he doesn't like, he may get deflated and think, "Ah man, she likes that show? There's no way she'll be into me now. Dammit, another prospect hasn't panned out. Story of my life. I'll never meet anyone."

They have a mindset where they expect the universe to deliver a girl to them

A lot of what I've mentioned so far hints at this. It's hard to explain, but almost unconsciously they can have the attitude that in order to get a girlfriend the world has to send them one packaged in such a way that they won't feel anxious or have to do anything that pushes them out of their comfort zone. They figure everything will finally work out one day when they just find themselves in a situation where they stumble into a girl who naturally likes them, who they won't have to approach to start talking to them, who they won't have to ask out, and who has the magic combination of qualities that he never feels nervous around her.

It's also really common for shyer guys to fantasize about meeting a really forward, aggressive girl who makes all the scary moves for them. She asks him out, she kisses him first, etc. However, if a guy is really shy he may still balk in the face of someone so direct, and still blow his chance.

The idea that if they want a girlfriend they'll have to actively work on finding one, or that they'll have to learn to cope with their nervousness, isn't on the map. Nope, they just have to meet the perfect girl under the perfect circumstances, where they'll essentially be guided along by rails the whole way with no room to screw up. They have thoughts such as: "Well I didn't meet any girls this semester. Maybe in next semester's classes I'll randomly end up sitting beside the person of my dreams", or "Maybe at my job the girl I like will be assigned to work on a project with me all day", or "Maybe if this time when I go to the bar and just stand around all night a girl will walk up to me and seduce me."

They can be pretty naive about what real relationships and interactions between the sexes are like

When a guy is shy and inexperienced with women he usually isn't immersed in female company or the dating and hook up scene. They may also be socially inexperienced or isolated in general, because they like to keep to themselves, or since they don't have a ton of friends. That means they get their ideas of what dating and girlfriends and relationships are like from sources such as movies, television, magazines, the internet, and snippets of conversation they've heard from other people.

Shy guys often develop a caricatured, romanticized view of relationships, because they've seen too many romantic comedies or high school dramas with Hollywood endings. According to their 'education' the beautiful cheerleader always wants a caring, sensitive guy who likes her for her. The female lead wants a nice guy to save her from the all the jerks she normally attracts. Women are sweet, innocent creatures that needed to be nurtured. Shy guys have a blind spot for the reality that some girls might get drunk and make out with a hot guy just for the hell of it, or that they could have a friend-with-benefits, or that they would want to casually date a few people at once, or that they could go home with someone they met that night at a party.

This can make shy guys a bit clueless about dating protocol. People in a guy's age group may not even really 'date' at all, but he wouldn't know it because that's what people do in the movies and on TV. They may wonder things like: "How exactly do you ask a girl out?", "Are you really supposed to have that first kiss on her doorstep at the end of the night like in the movies?", "Am I supposed to take her out for dinner and a show like I keep reading about?"

When they meet a girl they like their mind tends to jump to melodramatic fantasies

Continuing on the theme of having an over-romanticized view of dating: When a shy, inexperienced guy finds a girl he likes, his thoughts often aren't, "She seems neat, maybe we can hang out a few times and see where it goes." No, it's more likely to be, "She's the one. She's my dream girl. I just want to cuddle her by the ocean for hours as we watch the shooting stars above. Then we'll make sweet loving love... blah blah blah." Besides from being kind of cheesy and over the top, this thinking contributes to their nerves because they put too many expectations on things. The girl they've just noticed in class could be their lifelong soul mate. Boy, better not screw that one up.

They put too much focus on the girls they randomly meet as they go about their lives

Since they don't try to create their own options or prospects, whenever a half-decent girl comes into the life of a shy guy through school, work, or his social circle, his mind immediately leaps to, "Could this be the one??? Is this the girl who I'll end my streak of loneliness with?" They may start a new job, chat to one of their female co-workers about the weather for two minutes, and go home that night and daydream about dating her. They'll quickly get infatuated and preoccupied, constantly thinking if it's going to all work out with her.

What's weird is, objectively these girls often aren't even that appealing to the shy guy, or he obviously wouldn't be her type. However, because they have so few options, and are so desperate to meet someone, any minimally friendly girl they meet instantly becomes a possibility. They almost have to like these girls, what other choice do they have? If it later seems like things won't work out - which is common since he's often just invested a throwaway casual encounter with too much meaning - he'll get demoralized. But it won't be long before he's fixated on a new person.

I think girls should be aware that just by your being friendly, even in the most casual, offhanded way, to a shyer guy, he may start seeing you as a prospect. He may even get a somewhat obsessive crush on you. It's not that you sent him any signals, just that any girl he comes across offers a chance to end his Forever Alone status and his mind reacts to this a little too excitedly and desperately.

The obvious lessons

Here's what I think they are, maybe you can figure out some other ones:

That's all I've got. I hope this article helps you hook up with that cute, quiet, quirky guy you've got your eye on. And of course I hope this article indirectly makes life easier out there for all the shy dudes out there too.

Bonus section: Figuring out why a shy guy you're interested in is acting the way he is

This originally wasn't part of the article, but I decided to add it after several women wrote to me asking for help with a shy guy they were interested in getting to know. Overall their situation was that things seemed like they were heading in a promising direction, but then he starting avoiding contact with her, and she's not sure why he's acting that way or what she can do to salvage things. The little details of each story vary:

The hard part of figuring all this out is that while shy guys as a whole have certain tendencies, it's impossible to tell what any one of them is thinking in a particular situation. Any of these explanations could fit:

Since you can't expect a shy guy to do it himself, the best way to clear things up is to make a move of your own that forces him to give you a direct answer. If you've spoken, ask him out. If you've already gone on some dates, ask him if he'd like to go out again. If he hasn't talked to you yet, start a conversation. It may go well or go nowhere, but if he seems interested, but shy and hard to read, then ask him out. His response still won't necessarily reveal his motivations (he could be into you, but turn you down due to nerves), but at least you'll be able to move forward.

I realize this isn't the easiest thing to do. Making a move yourself may feel scary or unnatural. That goes double if you're on the shy side yourself. However, with really shy guys this comes with the territory. You never know if or when they'll get the guts to make a move themselves, so if you're really interested in seeing where it goes with him you've got to go for it.