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:

Logo
Zales
  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.  

KNOMO LONDON BACKPACKS  #THISISMYOFFICE

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

NO, DON'T ASK FOR HIS HELP OR INVITE HIM FOR COFFEE

Last month we talked about the difference between a Relationship (which has the potential to progress toward commitment) and an Entanglement (a permanently “casual” situation that can only lead around and down, never forward).

Past the age of 25, most women view entanglements as a painful waste of time and prefer to avoid them. You want to invest in a future with a man who cherishes you, not just "hang out" with a man who doesn't think you're worth locking down. If that’s where you’re at, I’ve got 2 practical steps you can follow to avoid ever getting involved in an entanglement. In this post we’ll talk about Step #1:

Step #1: A beautiful, desirable woman — that’s you —should never approach a man first, whether in real life or online.

Why you should never approach a man first

This is advice that feels right to many women. Yet, we allow ourselves to get talked out of what we know, intuitively, is natural and feminine. Modern culture doesn't always value authentic femininity. It is popular for friends, family, and dating experts to encourage you to take the initiative with men because those folks only listen half-way to what you say you want: more men, more dates, more attractive options.

It’s true: Making the first move with guys will DEFINITELY get you more action than passively waiting. It will get you out of that dry spell and into the arms of... men who just aren’t that into you. That’s why “you’ve got nothing to lose” advice doesn’t satisfy your deepest needs. Because no matter how lonely you may feel today, you don’t just want “more” experiences—more unreturned texts, more non-date hangouts leading to sex—you want quality experiences. That’s what you mean when you say you are tired of being single. You want to be loved by a man who sees you as his Forever And Always goddess, not just a Good Enough For Now girl.

So let’s dig into some truths about cool women — like you — making the first move with men:

FROM BCBG

#TRUTH 1 — Yes, asking for help is an approach.

Any action that gets you and him talking or texting is initiating contact. Just recognize it for what it is. If he didn’t walk over, call, or text first, then you made the first move.

#TRUTH 2 — No, approaching men first doesn’t convey confidence.

Instead, it suggests you don’t believe you are WORTH approaching. You lack confidence in your desirability. It’s the equivalent of sending yourself a dozen roses on Valentine’s Day. As if you think passionate male attention is for other, more beautiful/perfect/skinny/whatever women. In the end, taking on the guy’s role can actually make you feel worse about yourself as a woman. Not very empowering.

Zales

#TRUTH 3 — Yes, certain men will enjoy it when you make things easy for them.

Men who aren’t truly available — married or otherwise taken — prefer to take a passive approach to finding fun on the side. Aggressive chasing is too risky for a cheater, and he feels less guilty if you are the one to initiate pursuit. Likewise, you may be successful with bored single men looking for a distraction, or lonely guys who appreciate your effort but who will never be starry-eyed over you.

#TRUTH 4 — No, you won’t miss out on legit, nice, shy guys if you stop pursuing men.

I think shy, awkward, nerdy men are totally hot — so much so that I married one. So believe me when I tell you that you never have to make the first move with a shy guy. Approaching a pretty woman is like a really hard math puzzle — smart men thrive on the challenge and keep trying until the problem is solved. If he wants you badly enough, even the most clueless dude will eventually figure out how to get you one-on-one.

#TRUTH 5 – Yes, you may end up going on fewer dates than your friends.

You know that co-worker who messages every cute guy she sees on POF? Maybe she enjoys the drama and anxiety of never knowing where she stands with those men—but probably she doesn’t. Maybe she’s just afraid that if she doesn’t make an effort she’ll “miss out” on some Prince Charming. Instead, value quality over quantity.

Look, sometimes you just have to be a rebel: stop doing what everyone else is doing. Well-meaning people think they are helping you when they say you should just "get closure" with that cute guy you've been crushing on for months. Instead, stick to The Rules of dating. Let men approach you first. This is the first and most important way to make sure you never, ever, find yourself wasting time with someone who doesn't truly value and appreciate all that you are. 

Robyn Wahlgast is a Rules Certified Dating and Relationship Coach for Women, and a happily married mother of three. Need advice about your own relationship? Consider booking a private consultation with Robyn. Never miss a new blog post: subscribe to our FREE newsletter.

ROBYN ORIGINALLY CREATED THIS ARTICLE, WITH LOVE, FOR MICHAEL FIORE'S DIGITAL ROMANCE