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

This site doesn't go into dating advice, 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 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 describe a guy who's really, really inhibited and awkward around women. Not all shy men deal with issues that intense or will have every characteristic apply to them. 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 men say they think.

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

Shy guys are 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 a little nervous when they have to ask a woman out, make a move to 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. 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 it's like an invisible force field is preventing them from doing so.

Shy guys are especially 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 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 her for whatever mysterious reason. At other time they can force themselves to do it, but they're a total mess 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 woman, 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 is that when they first run into that woman she's new and they haven't had time to overthink things and develop any nervous feelings for her. 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:

• He's too nervous to talk to her again
• He does talk to her, but is such a withdrawn, obvious wreck that she's not interested
• He talks to her, but is too nervous to be himself, ends up acting like a goofball, and shoots himself in the foot
• He's so nervous that at that immediate moment escaping the anxious symptoms takes precedence over anything else, and he acts rude, odd, aloof to purposely sabotage his chance

This 'setting them up, but not following through' scenario can happen to different degrees. The first is when a guy simply sees a woman around a few times and makes confident eye contact with her. She seems attracted and intrigued and like she's waiting for him 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 woman, say because he randomly 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 woman 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 women out

Sometimes a guy will be able to talk to a woman he's interested in, often because the circumstances put them together so the onus wasn't on him to approach anyone. If he likes someone he'll often feel too nervous to ask her out and face the awkwardness and risk of rejection that entails. He may never invite her on a date, or put it off so long that by the time he does the moment has passed.

They're nervous about making a move

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

He may have a blatant, all-systems-go opportunity where the woman is clearly interested, but he can't manage to go through with it. There he is, sitting on a couch watching a movie with his 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 says he better drive home before it gets too late. Afterward 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 if they're sexually inexperienced is that their embarrassing secret will be outed, and they'll be humiliated. They may think something like, "I've never kissed a woman. 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 women they perceive as being more 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 woman 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 shy men in two ways. First, they'll often rule out more-obviously experienced women as prospects. Too scary. Only harmless, innocent-seeming women don't arouse their fears. But there are only so many women out there who are just as shy 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 he's into a woman, and she seems into him, and she says something that draws attention to her comparatively higher level of experience (e.g., mentioning an ex-boyfriend), he may 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'd 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 dating game as early as everyone else.

They're insecure and hard on themselves about dating

When a guy is shy and unconfident about his love life insecure thoughts often flow through his head 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 woman 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 super-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 woman 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 hope the universe will deliver a partner to them

A lot of what I've mentioned so far hints at this. Almost unconsciously shy guys 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 stumble onto a woman who naturally likes them, who they won't have to take the initiative to talk to, who they won't have to ask out, and who has the magic combination of qualities which ensures he never feels nervous around her.

It's also really common for shyer guys to fantasize about meeting a really forward, take charge woman 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 miss 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 woman under the perfect circumstances, where they'll be guided by rails with no room to screw up. They have thoughts such as: "Well I didn't meet any women 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 woman I like will be assigned to work on a project with me all day", or "Maybe this time when I go to the bar and just stand around all night a woman will walk up 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. He may also be socially inexperienced or isolated in general, because he likes to keep to himself or doesn't have a ton of friends. That means shy guys get their ideas of what dating and relationships are like from sources like movies, TV shows, the internet, and snippets of conversation they've heard from other people.

Shy guys can 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 need to be nurtured. Shy guys have a blind spot for the reality that some women 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.

This can make shy guys pretty clueless about dating protocol. People in a guy's age group may not even really "date" in the classic sense 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 woman out?", "Are you really supposed to have that first kiss on her doorstep at the end of the night?", "Am I supposed to take her out for dinner and a movie?"

When they meet a woman 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 woman he likes, his thoughts often aren't, "She seems fun. 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." Besides from being kind of cheesy and over the top, this thinking contributes to their nerves because it puts too many expectations on things - The woman they've just noticed in class could be their soul mate. Boy, better not screw that one up.

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

Since they don't try to create their own options, whenever a half-decent woman 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 woman 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 wondering if it's going to all work out with her.

What's weird is, objectively these women 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 woman they meet instantly becomes a possibility. They almost have to like these women, what other choice do they have? If it later seems like things won't work out - which is likely since he's just invested a throwaway casual interaction with too much meaning - he'll get demoralized. But it won't be long before he's fixated on a new person.

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

Some shy guys can become bitter and resentful toward women

Most of this article has described a sweet, naive flavor of shy guy, but I had to cover this darker point too.

Not every man who's shy and inexperienced with women eventually becomes a hateful misogynist. Some are well-adjusted, healthy people, aside from their nerves around dating. Some stay wholesome and innocent in their attitude about relationships. But a few can go down an angrier road after feeling like they've failed in their love lives for too long.

Some common themes in their anger:

• "Women have it way easier in the dating world."
• "Attractive women have it easier in life, and often use their looks to get things they don't deserve."
• "Women have bad, shallow, irrational taste in the men, i.e., they're only into buff douchebags."
• "Women have entitled, unrealistic standards for men."
• "Women are generally childish and overly emotional."
• "Women are immature, manipulative game players."
• "Women can be awful and cruel to guys they don't find up to their standards."
• "Women will heartlessly use men."

I think guys who have been actively picked on and rejected by women growing up are likelier to become angry at them. That's opposed to shy dudes who have flown under the radar, or even had plenty of interest and opportunities they just didn't have the guts to act on. Of course, it's not just inexperienced, awkward men who can become bitter sexists. Guys who sleep around a lot aren't exactly known for their enlightened attitudes toward women.

You can't always tell, but often if you talk to a shy guy long enough you'll be able to tell if he's of the resentful variety. He may have a slightly hostile vibe, or it won't be long before he makes a questionable chauvanistic remark. You've probably lost any interest you might have had at this point. If you're speaking with a man and your gut tells you he's a decent person, but just hasn't dated much, it's often right.

The obvious lessons

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

• If you want to get to know a shy guy, it may be easier to talk to him yourself.
• If he seems awkward, be persistent and try talking to him again a few more times.
• If you seemed to hit it off with a guy, but now he's acting strange and hesitant to talk to you, he may be shy (or it could be for any of the other reasons two people seem to hit it off but then one doesn't follow up on it...)
• If a guy is nervous or insecure around you for whatever reason, just cut him some slack, don't draw attention to it, and he'll calm down eventually.
• Even though you may be sending obvious hints, and even if he does understand them, you can't necessarily count on him to ask you out or kiss you himself. It may be easier for all involved if you make the first move.
• Don't expect a shyer guy to necessarily get concepts like, "We just hung out twice, and fooled around once, that doesn't mean we're a couple now." He could be too naive or romantic to get it.
• If you think a guy you like is inexperienced then do him a favor and do nothing whatsoever to draw attention to it. Don't give him an opportunity to get all freaked out and insecure over what a supposed pathetic virgin he is.
• If you think a guy is inexperienced, you may want to take the same approach to your own past experiences. Just don't bring them up and potentially give him something to worry about. Sure, after you've messed around a bit and he's more relaxed and comfortable with himself you can bring up your ex-boyfriends or what you like in bed, but before that it's probably better to take a "If he doesn't know about it, it won't bother him" approach.

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:

• Sometimes it's obvious the guy is shy, while at other times he's harder to read and she's wondering if shyness explains his behavior.
• Usually the promising first contact is that she sees the guy around in her day-to-day life - at work, on the bus, at her usual coffee shop, at the gym, etc. She's either briefly chatted to him on a handful of occasions, or they've just locked eyes a few times. She gets the sense he's interested. He seems happy to see her, but also gets flustered and tongue-tied in her presence.
• The second type of promising initial contact is they've been on a date or two. Things seem to be going well, and he comes across as interested, but also nervous. He may have had a giant green light to make a physical move but didn't take it.
• When the first type of contact goes south what happens is rather than show more interest/ask her on a date/come talk to her, he suddenly starts blanking her out. If she sees him as she gets on the bus he quickly looks away. If she tries to chat to him by the elevator at work he gets uncomfortable and quickly ends the conversation.
• If they've gone on a few dates, he stops responding to her texts and calls.

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:

• He's interested in you, but too shy to make the first move.
• He's interested in you, but decided he's blown it (e.g., "I've caught her eye twice now in the coffee shop and haven't had the guts to say hello. She must think I'm a huge creep", "I wimped out of kissing her at the end of the second date. Why am I so spineless? No woman likes guys like that.") Now he feels ashamed and extra-awkward around you and is trying to make the whole thing go away.
• He's interested, and was fairly calm the first few times you saw him, but now he's feeling the pressure and it's made him too nervous to take it any further.
• He's shy, was interested at first, but changed his mind. His shyness is causing him to act weird around you. He's not able to let you down in a polite, straightforward way.
• He's not shy, was interested at first, but changed his mind. His behavior isn't due to shyness. It's just the standard insensitive tactic of ignoring someone you're not into until they move on.
• Shy or not, he was never interested, and you read something into your interactions with him that wasn't there. He's realized you feel that way and it's making him act clumsy and evasive.

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.