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.

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. My advice will make a lot more sense if you're already familiar with the basic concept of 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.   

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?”

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.

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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.

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"Like a beautiful butterfly she shimmers just out of reach." - Robyn Wahlgast

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. 

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?

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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.  

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."

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.  

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.

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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