HOW TO DATE A SHY GUY (UNDERSTANDING MEN)

Many of us, it seems, like shy guys. (I like smart, nerdy, shy guys so much, I married one.) It's not surprising: these men tend to be quiet leaders — successful and widely respected. There is an art to dating introverted men, though, and this article will help you decide if this personality type is your best match. The good news is that you don't need to be an introvert to date one. But to keep your romantic energy in balance, you will want to follow some basic rules.

Many women mistakenly assume that being overly friendly and “easy to get will reassure the Shy Guy. Nothing could be further from the truth.

FROM E.L.F.

Many women mistakenly assume that being overly friendly and "easy to get" will reassure the Shy Guy. Nothing could be further from the truth. Being "easy" and laying everything out on a plate will actually make him retreat further into his shell. You'll be pursuing him, so your energy will shift from being feminine to masculine, and that's not healthy or sexy (for you or for him) in the long run. Relationships that start out with this dynamic never really recover, and as months and years pass, you may find yourself in a sexless "just friends"/ roommate arrangement.

how to date a shy guy

If you are crushing on a shy guy, I definitely recommend that you read The Rules, by Ellen Fein and Sherrie Schneider. The Rules are a great, step-by-step introduction toward letting a man lead and set the pace of the relationship.

Regardless of personality type, men are happiest when allowed to discover love at their own pace. If the relationship moves forward, it's because he chooses and wants to lead toward commitment. If a man tends toward an introverted personality, it’s even more important that you let him lead. Extroverts can hold their own and fight fire with fire. But if you admire a man with a more subtle style, you have to be careful not to overwhelm him with your eagerness, or nudge him into "going along" passively with your agenda. You could find yourself in an entanglement with a man who's not really sure how or why he got there.   

FROM ASTRID & MIYU

Always let him lead. Don't get tangled up with a man who's not sure how or why he got there.

Here are 7 observations and comments from clients over the past year. See if any of these situations sound familiar:

  1. “I really like this guy at work, but if I don't suggest it we'll never actually go on a date.”
  2. “The guy I’m interested in doesn’t seem to know what he’s supposed to do to date me.”
  3. “The Rules describe an old-fashioned way of dating that doesn’t exist anymore.”
  4. “Men my age don’t know how to date.”
  5. “My crush is really shy. His ex-wife really messed him up. I can only do some of The Rules with him.”
  6. “If I want him to treat me like a lady I have to tell him what to do every step of the way.”
  7. “We’re both grown-ups. I know he doesn’t want to play games and neither do I. Shouldn't I make an exception for him?”

FROM DR. BRANDT

The Secret

If you identify with any of these situations, I will let you in on a secret: the “problem” in each of these scenarios is not that the man is shy or inexperienced. The underlying issue is that he is just not interested enough in starting up a relationship with that particular woman.

Guys who aren’t THAT into you may still sleep with you and hang out” with you if you make it easy. Is that what you want?

Sure, he’d be okay with having casual sex with her and hanging out until something better comes along. But I don’t know many women who enjoy being the good-enough-for-now option. If each woman in situations 1 - 7 were to get the ball rolling herself, or help the man date her and make excuses for his behavior, she would simply be prolonging the agony of being in a go-nowhere entanglement. That's not "dating a shy man," that's accepting crumbs from a guy who is just killing time.

That's not “dating a shy man. That's accepting crumbs from a guy who is just killing time.

Let’s go through these scenarios, one by one, and note the difference between a true Shy Guy and one whose feelings are simply lukewarm:

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  1. “I really like this guy at work, but if I don't suggest it we'll never actually go on a date.” My take: As I’ve written many times before, you should never make the first move or ask a man out IF what you want is a long-term relationship leading to marriage. All the reasons are here. Shy guys DO approach, date, and marry women when they feel motivated to do so.
  2. “The guy I’m interested in doesn’t seem to know what he’s supposed to do to date me.” My take: Men are incredibly resourceful when there’s a problem that needs to be solved. Whether his car is making a weird noise or the latest iPhone update wiped all his data — he will head over to YouTube and learn how to fix it. If he really wants to ask you out / impress you / propose, he has a million ways to figure out how.
  3. “The Rules describe an old-fashioned way of dating that doesn’t exist anymore.” My take: If you are consistently meeting men who only want to hang out or “cook dinner” at his place, and not go out on proper dates, then you have two choices: 1) Just say no to hang-out dates and see if he offers an alternative; 2) Learn how to screen men better. If you’re online dating, these tips will help you screen out players and other guys who want to keep things permanently casual. 
  4. “Men my age don’t know how to date.” My take: Women in every age category can feel like their situation is the worst. As a dating coach I know first-hand that you all have an equal shot at meeting your Mr. Right — at any age. Consider dating men who are 5-7 years older than you, if you're just going around in circles with men your own age or younger. Remember: men are resourceful. If he’s interested enough to learn what your standards are, he can figure out how to meet them.
  5. “My crush is really shy. His ex-wife really messed him up. I can only do some of The Rules with him.” My take: When a man heaps all the blame for a break-up on his ex, consider it a Buyer Beware. Just keep your eyes open, guard your heart, and do The Rules. No exceptions.
  6. “If I want him to treat me like a lady I have to tell him what to do every step of the way.” My take: Make sure you are taking good care of yourself. Dress your best, be your best, and say No to any behavior you don’t like. Men will make the effort to figure out what you want if they like you enough to do so. Whatever you do, don’t micromanage your date. Just move on if he has decided you aren’t worth investing in.
  7. “We’re both grown-ups. I know he doesn’t want to play games and neither do I. Shouldn't I make an exception for him?” My take: Date with an open heart and strict boundaries. That’s what emotionally healthy men and women do. But you still have to pace the relationship so that the initial spark has time to develop into deeper feelings. It’s unreasonable to expect instant bonding over that first glass of Merlot. Doing The Rules allows you both to take your time.

Men are resourceful. Whether his car is making a weird noise or the latest iPhone update wiped all his data — he will head over to YouTube and learn how to fix it. If he really wants to impress you, he has a million ways to figure out how.

As Rules women know, we don’t “do the rules” on men. We do The Rules on ourselves, stripping away negative behaviors and replacing them with healthy behaviors that naturally allow attraction to build. The Rules definitely do work within any relationship, with any man. If a man isn’t a good fit for you, The Rules will “work” by revealing early on that you are incompatible. That may seem like a disappointing result at first, but it's a powerful gift in the long run. 

e.l.f. cosmetics

Sometimes The Rules work by eliminating incompatible men from your life. That's a powerful gift in the long run.

Since you’re not approaching men (by asking for their help or inviting them for coffee), the rules will help you avoid players and pick-up artists as well as looky-loos—dudes who stare at you or flirt or “favorite” your online profile, but who never actually ask you out. You won’t get caught up in go-nowhere entanglements or affairs with unavailable men.

So how should you behave with a truly “shy” or inexperienced man?

The best way to deal with an introvert is to match his actions and level of interest. And then dial it back even further. Don't lean in lean back. If you are naturally an extrovert, that's cool. You don't need to pretend to be an introvert in order to attract one. Always bring your unique vibe to the dating game. Dial down your effort, not your charm. Study my flirting tips if you want to know how to enchant a man who tends toward a more subtle, quiet personality. WAIT until he asks you out – don’t make the first move. And once you’re on a date, make sure you show him your most feminine, vulnerable qualities.  

FROM BEAUTY BRANDS

Dial down your effort, not your charm.

The inexperienced man is very often a diamond in the rough and will make a wonderful partner in the long run. He may have been married previously or in a series of long-term relationships — he likes and values female companionship — but he hasn’t dated much in a formal sense, and seems confused or tentative when dealing with women in a romantic setting. 

The inexperienced” man could be someone who married his high school sweetheart and now, years later, finds himself single. He values female companionship but has little formal dating experience.

Because he appears to need help in approaching you and setting up dates, you might be tempted to bend rules for him or to assume that he is an exception to the rules. That would be a mistake. He may appear to be passive, but that’s usually just a temporary switch that got flipped by the various women in his life — his overly helpful sister, exes, and coworkers. Remember: If a bachelor has a steady job and is reasonably well-groomed and moderately attractive, then he has women approaching him at the gym, at work, contacting him first on POF and eHarmony, and generally showing him attention. He may be surrounded by a near-harem of female "helpers."

FROM BCBG

The shy” or inexperienced man is like a turtle: when women chase after him he retreats deeper into his shell.

When a man is used to being guided and micromanaged by women, it can become a behavioral pattern that is both comfortable for him and hard to break. That doesn’t mean he is satisfied or happy with that dynamic, or that he isn't capable of pursuing you if he’s motivated to do so. The inexperienced man is like a turtle: when women chase after him he retreats deeper into his shell. What he responds to best is a woman with a light, feminine touch; like a beautiful butterfly, she shimmers just out of reach. By not “helping” him date you, you are letting him know that you see him as the competent adult man that he is. That may be a message he is starved to hear. If he approaches you and you start dating, trust that he can figure out what to do. Your confidence in him will inspire him to do his best. If he is paying attention and trying to learn your preferences, then he is a keeper.  

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KNOMO LONDON BACKPACKS #THISISMYOFFICE

What he responds to best is a woman with a light, feminine touch. Like a beautiful butterfly, she shimmers just out of reach.

His lapses into "helpless" dating behavior may tempt you to grab the steering wheel. Don't do it. Just relax, take a break with your girlfriends, and trust that your faith in him will bring out his inner Gentlemen’s Rules.  

The shy” man wants to be with a woman who trusts him to give her his best.

You don’t need to bend rules or weaken your boundaries in order to attract a particular man. In fact, if you feel like you have to break rules to get things started or to keep a relationship going, something is wrong — he's not truly interested or available. There is a real art to dating the inexperienced man — some women just lose steam (and confidence) with this guy, while others blossom as his attraction and drive builds. The next time you find yourself struggling to be Rulesy, mentally lighten up and visualize yourself as that beautiful butterfly. If it's still not working, consider that you may simply be dating a man whose style isn’t compatible with yours. The kindest action you can take is to release him to date others while you continue to search for your best match.

Robyn Wahlgast is a Rules Certified Dating and Relationship Coach for Women. Need advice about your own dating situation? Consider booking a private consultation with Robyn. Never miss a new blog post: subscribe to our FREE newsletter

ROBYN'S TOP 5 TIPS ON DOING THE RULES

Do you need to treat him mean to keep him keen?

hi Robyn,
I am just starting out with The Rules and I keep hearing about bootcamp rules and strict rules. How do I know if I’m being strict enough and when would I want to be bootcamp? My gf says I should be b*tchier with guys, but I’m not sure.
Thanks,

Rachael

READ FIRST: ALL ABOUT "THE RULES"

ROBYN'S TOP 5 TIPS ON DOING THE RULES

This is an email I recently received from a new subscriber, and it reminded me how much confusion there is around doing the Rules successfully. If you’re reading this blog and you’re not sure what The Rules are, check out www.therulesbook.com to learn more about The Rules book and its updated version, Not Your Mother’s Rules, by authors Ellen Fein and Sherrie Schneider.

Do you need to treat him mean to keep him keen?

FROM DR. BRANDT

Tip #1: The chase should be fun — for him and for you.

I like to say that if a woman is going to do The Rules she should do them exactly as written rather than “strictly” because some women go too far and actually act strict, like a sour old granny. That’s not very sexy. You want to ignite a chase, and the chase should be fun — for him and for you.

TIP: If you can do The Rules strictly and be a pleasure to be with, you are a Rules Girl.   

Some girls get the idea that they should act like b*tches to appear challenging and not-so-easy. Understandably, these women want to communicate that they have strong boundaries, so that they will be treated well. Unfortunately, being deliberately difficult often has the reverse effect: it signals that you are on guard and worried about being [pick one]:

  • Stood up
  • Cheated on
  • Abandoned
  • Forgotten

Instead, practice channeling the serenity of a woman who is always respected and cherished in relationships. (You don't know there's any other way!) Emotionally healthy women are mysterious but real on dates. (See Tip #5)

Your mindset: I have nothing to worry about. Men always treat me well.

FROM BEAUTY BRANDS

If you want to marry a quality man — someone who has his act together personally and professionally, and who is open to love — then you want to project the right qualities. The rules woman should be light and breezy, and a pleasure to be with; she has poise and great manners. She is deeply feminine and also easy to connect with. She's not closed off, bitter, or angry. She likes men! She's not nervously looking over her shoulder, waiting for her new guy to disappoint her.

TIP: The Rules woman likes men. She's not nervously looking over her shoulder, waiting for her new guy to disappoint her.

Tip #2: Do all the Rules, all the time.

This is a really important point, because to do the rules well, you’ll want to apply them to all areas of your life. You will have a hard time being rulesy on your dates if you have poor boundaries at work or with your kids and family. Learn to use the rules in a way that naturally fits your personality, and you will be able to practice them all the time. I don’t know many professional environments in which being cold, unapproachable, and mean are great career-building qualities. Mind your own business and avoid gossip and negativity — that’s part of doing the rules at work — and interact with your colleagues in a kind and pleasant way. You will have many more opportunities in life if you choose to live graciously and with good manners.

I get calls from women who have given up on the rules because they have trouble doing them consistently. They might start out in a rules relationship and then let things slide as they mistakenly believe it’s time to be “real” with a boyfriend (i.e., stop doing the rules); or they simply can’t keep it up past the early stages of a relationship. If you focus on being yourself—the best, most confident version of yourself —you may find it easier to do the rules consistently, with everyone, and that’s the best way to internalize healthy boundaries.

FROM BCBG

Tip #3: Confidence is cool, but poise has more power.

Just as men who loudly flaunt their successes can seem insecure — the opposite of what they hope to project — the mean girl is also less desirable than a woman who quietly radiates true inner confidence. I have seen women go overboard at singles events or in clubs, trying to seem disinterested and aloof, or bantering with men in a rude manner. Instead of seeming cool these girls are just awkward. Understand that if a man finds you physically attractive, he will pursue you regardless of how grumpy or ill-mannered you are — for short-term fun. The problem is that you won’t attract and retain a quality guy who will want to bring you into his life for keeps. Don't be a player's prize for the night.

"When I'm at a club or party, I head straight for the meanest girl cuz I know she's easy, lol. She is fronting but underneath she's been hurt... Lots of these girls have a sad story, they've been dumped and used."
 — Darius (age 26)
"Real men don't love b*tches. But we'll sleep with one if she's hot. ;)"
— Mike (age 37)

Marriage-minded men are looking for a woman who is naturally poised and relaxed. You will instantly signal quality if you practice an open and quiet confidence when you are in social settings. Always listen more than you speak, and you will not seem nervous — even if you have first-date jitters. Fully accepting and being at peace with who you are is an essential part of your beauty. Successful men choose wives who can handle themselves in any social setting and who are gifted at connecting people (this is just a hard-wired preference). Interacting easily with those around you can help you attract your Mr. Right. 

FROM E.L.F.

Tip #4: Be a Bootcamp Beauty Queen.

Bootcamp Rules (the strictest interpretation of the official Rules) can help the “overly nice, gushy girl” present a stronger, more balanced personality. However, the effect should be more Beauty Queen than Sour Old Granny. We're not trying to punish men. As always, you'll want to bring a fresh and feminine spirit to your behavior.

TIP: If you're not normally bootcamp, and you feel the need to suddenly become super-strict with a man who is not treating you well, this may be a red flag.

There is one scenario where bootcamp rules can't help, and that is if you’re dating Mr. Wrong. If you feel the need to be bootcamp with your guy, it could mean that deep down, you don’t trust him. Be careful that you aren’t simply delaying the inevitable. If you’ve caught him cheating on you or otherwise truly disrespecting you, he is not your Mr. Right, and bootcamp rules are not going to change that. The rules say to move on — not to invest more time and energy in a man who doesn’t love you.

Finally, don't overlook the power of feminine vulnerability. In fact, a man simply can't fall in love with you — not in a deep, lasting way — if he doesn't first feel protective toward you. Make sure you show him your softer side as you do bootcamp rules, so that he can fully connect with you. 

Tip #5: Be Real.

Connecting with another person is exciting. It's a first date... you make eye contact mid-sentence... and you just kind of know: this person is my kind, my tribe. Men crave this jolt of emotional connection just as much as women do. In fact, if it's not there at all, he will get bored and eventually move on. (Amazingly beautiful women are sometimes left on sidelines of love, for exactly this reason.) 

Being mysterious includes having depth. (To be holding back, you have to have something to hold back!) When your manner suggests that there is much to know about you... that's when you create true intrigue. That's when a man becomes interested in knowing more. That's the beginning of a chase that leads to lasting love, not just sex.

TIP: When a woman combines the mystery of The Rules with a genuine realness and presence, there is no limit to her ability to enchant men.   

Remember, The Rules are like vitamins: in the right dose they are healthy and positive; but don’t assume that doing more than is necessary or taking them to extremes will get you a better result. Be hard to get—but not impossible to get. Do the rules as written, with warmth and charm, and you’ll be attractive and confident in all areas of your life. All of us are capable of achieving the inner radiance that comes from being a Rules woman.

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Robyn Wahlgast is a Rules Certified Dating and Relationship Coach for Women. Book a private consultation or subscribe to her FREE dating and relationship newsletter and get priority access to all new content.