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Ask The Good Enough Guy: I’m Too Shy To Talk To Men!

Hey Will:

I hope you can help me. I’m a single woman in her 30’s, not married and if something doesn’t change, will remain that way for many years to come. See, I just don’t know what to say to a guy I think is cute. Here’s an example.

The other day, I was at a charity event and I spied a nice looking guy. He had a poster and was asking people to sign it in support of the cause. So I stopped to sign it; heck, he even held my dog while I did it. But when I was done, I handed him the pen and walked away. I looked back and caught him looking at me. Perfect opportunity, right? Did I do anything? No!

Another time I met a guy and we happen to have several mutual friends (I found this out on Facebook). But now what? Should I ask our mutual friends to get us together? Or is that too much like high school?

I’m terrified of making a fool of myself. What if I ask a man out and he’s married? Or gay? Then what do I do? I hate this because I’m petrified and like I said, at this rate, I’ll be alone forever.

Will, you’re a guy’s guy. What would you want to hear from a woman in a situation like this? And does making the first move sound too forward?

Dateless in Dayton

Hey DiD,

Huh? Are you serious? You don’t know what to say to a guy? What’s there to say? All you have to do is give him the ok and let him worry about what to say. I’ve sat in a room full of guys who were pitching opening/pick-up lines to each other, trying to figure out the best ones to use at the club later that night. That’s the God’s honest truth. It‘s what guys do. Let them worry about the sales pitch; you just need to learn to open the door when they’re knocking.

What you need to know is that women almost always make the first move, it’s just hardly ever spoken. Guys are just waiting on a green light and we don’t need you to speak; just give us a sign. Back in my single days, I had what I called the “Three Glance Rule.” If a woman looked at me once, she was noticing me. If I got a second look, it meant she might be interested, that’s a yellow light, proceed with caution. But if I got a third look, it was on! And this was just from a look! That rule served me well about 90% of the time (hey, no rule’s perfect!).

WHAT TO DO: Guys aren’t waiting for your opening line, we’re waiting for a chance to use ours. If a woman does any of these non-verbal signs:

-Makes eye contact
-Smiles at us
-Flips her hair
-Licks her lips (or nibbles her lip or… well, pretty much any mouth thing.)
-Whispers to her friend while looking at us
-Touches our arm, shoulder, back, or any other part of us
-Giggles at something we’ve said
-Brushes past us as she walks by
-Winks at us
-Or (obviously) motions for us to come to her

…we assume she wants us to approach and we do. And if we’re wrong, so what? The average guy is lucky if he gets one date for every four times he crashes and burns (not a proven percentage; but it’s what I remember and still see in my single friends).

So what should you do? Practice! I listed ten ways to get a guy’s attention and I’M A GUY. Your female friends will know a hundred more. But having a full arsenal is useless unless you go out for some target practice. Now you may want to try this stuff in a mirror at home first, if you’re worried your wink will look like you lost a contact lens or your lip bite will just look like you’re hungry (of course, that may not be a bad thing either). This is pretty simple stuff, and trust me, you can’t give the wrong sign to the right guy. Just try the ones I gave you, try some of the ones your friends use, then perfect the ones you feel most comfortable with. Remember: this is all a game; possibly the oldest game in the world. Have fun with it!

WHAT TO SAY: If you absolutely have to speak (which you don’t), keep it short, light, and cute, and then combine it with something non-verbal. Let the situation dictate. For instance:

– If he’s in great shape, you say, “You have nice arms”… then do a lip bite and a giggle.
-If he’s intellectual, say “You look familiar, are you a writer?”… then do the eye contact, hair flip.
-If he’s a talker, say “I could listen to your stories all night” then wink…giggle…whisper to friend.
(Childish? Of course. Why do you think they call it “the game”?)

Remember that guy with the poster? If you had said, “Here’s my name, do you want my phone number too?” and given him a wink and a smile, he’d probably have his feet on your coffee table right now. And that cute friend-of-a-friend on Facebook? Just replace the giggle and a wink with LOL and 😉 New technology, same old game. So definitely have you friends play match maker. Yes, it’s like high school, but the reason we did it in high school was because IT WORKED.

As they say, “There are plenty of fish in the sea” and now that you have the right bait and know how to use it, throw in your line! Oh and if you come across a married fish or a gay fish once in a while, so what? Toss’em back and keep on fishing. Your guy is out there somewhere; don’t keep him waiting. Good luck!

Do you have a question for the Good Enough Guy? He can take it on! Click here and Rene will get it to him!

William Jones is originally from the tiny town of Alton, Illinois, and now lives in the tinier town of Reisterstown, Maryland. He is a happy husband and a proud father of three, and writes as a hobby, in those few moments he finds between husbanding and daddy-ing.


  1. Cody Williams

    November 5, 2011 at 10:13 am

    Dang, Will,

    You mean that’s what all those winks and smiles and batting of the eyes from women I run into meant? No wonder I’m still single. LOL.

    Actually man, I really liked your answer for a lot of reasons. I’m glad you told her to do it the old fashioned way. They way it’s been done since the beginning of time.

    I’m one guy who does not like it when women step to me like a guy steps to women. Don’t like it when they are too aggressive.

    However, to add one to your list I am super impressed when I woman sends me a drink. In a major way. She does that and I’ll marry her. In fact, I did once.

    Good advice.

  2. Tania

    November 5, 2011 at 10:49 am

    Enlightening. Let the flirting begin…

  3. Will Jones

    November 5, 2011 at 11:30 am

    Cody- Yeah, the “send a drink” one is good, but it only works in a bar or a club, and if this lady is just learning to dog-paddle, she doesn’t need to be in with the sharks just yet.

    And I completely agree with you about having a woman step to you like a man. Over-anxious comes off as desperate, and desperate can lead to stalker… and there’s no such thing as a sexy stalker.

    It’s funny you mention how often these signs are missed by men, though. That’s why a brother need a good wing man; his job is to watch for the signals that you miss! 😉

    Tania- What’s you’re best flirting move?… if you can tell us without having to kill us.

  4. Looking in Dallas

    November 5, 2011 at 1:03 pm

    Wow! I am older than 30 divorced for a while, let me repeat for a while and been out of a long term relationship for about 3 years. So I now feel capable of venturing out again. I’ve received much of the same attention that Dateless in Dayton has received and unsure how to respond. So thanks! I, too, have a question, and this may have been a past topic, but how guys feels about ladies that are sporting their natural hair. I love mine and I really don’t want to go back to a relaxer or get a weave to get a man. What can you tell me?

  5. Tania

    November 5, 2011 at 3:16 pm

    Will, the chick above is a lot like me. I’m afraid of rejection. I wait for the first move that seldom ever comes hence my singleness.
    The advice you gave above, I thought in so doing, was forward and a little aggresive but I trust if you say go for it…heck I will.
    I don’t drink and don’t really go to bars but I will and have no problems sending one to the cuty at the end of the bar. 😉

  6. Elizabeth Betrand

    November 5, 2011 at 4:09 pm

    Interesting tips, Will. I’m not much of a flirting kind of girl. But, most men know when I am interested in them by the attention that I give to them. For example, if I’m talking to you and I tend to touch your hand, your shoulder or even offer to share my food with you while we’re eating, those are signs that I am taken an interest in that person and want to get to know them better. The ultimate tip is if I leave you with my number, that’s an indication that I am open to have an extended conversation with that person to get to know them further.

    As far as making the first move, I don’t think I’ve ever asked a man to dance or to buy them a drink. Not saying I never would, but I’ve never done it.

    The best flirting tip is to be direct, because subliminal messages could be confusing and misinterpreted. I’ve told a guy that I would be open to seeing them or getting to know them more. I don’t think that’s too agressive. We’re grown folks. There’s nothing wrong with openingly expressing to a person that you find them interesting and want to get to know them more. This is my flirting tip – be direct in a tactful way.

  7. Elizabeth Betrand

    November 5, 2011 at 4:18 pm

    @Tania, I hear ya! I’m a traditional gal. I usually wait for the first move as well. And a guy wouldn’t normally meet in a bar, because I don’t drink. But, I have in conversation said, “I look forward to speaking to you again.” And usually, not all the time, an extended conversation follows – exchange of numbers.

  8. Chasing Joy

    November 5, 2011 at 6:20 pm

    I read this article just in time. I was actually feeling a little down regarding my single status. I am also like the lady who posed the question. I grew up to old fashioned parents and only brothers so I missed some of those teen year flirting lessons. Thanks for specefic tips. I will be trying some of them when I go out tonight. I may even get my courge up and send a drink.

  9. Will Jones

    November 7, 2011 at 1:38 pm


    I would NEVER suggest going to a bar to meet guys. I’m not saying there a no good guys there, but bars are the Walmart of the dating scene: you might find what you want, but there’s a better chance of you taking something home and wishing you hadn’t in the morning.

    If you want the right man for you, figure out what he’d be doing and go where he’d be. If you want a guy that likes dogs, he’s at the dogpark. A guy that’s good with his hands is at Home Depot. Guys that jog are out jogging. Hikers are out hiking. Unless you really want a guy that likes to try to pick up women; then, yeah, he’s at the bar.

  10. m.e. johnson

    November 7, 2011 at 2:39 pm

    Alrighty then, Will. Tried and true says the expert here. What’s really neat is locking eyes across a crowded room and he doesn’t stop until he is by your side.

    Don’t laugh people but I suggest watching a WWII love story. See how those nice, girl-next-door types work it. 🙂

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