5 Dating Tips for Shy Guys

Man and woman standing and laughing
Dating doesn't have to be painful and awkward.

If you read the comic strip "Peanuts," you probably know about the little red-haired girl. She's Charlie Brown's unnamed, unseen dream girl. Charlie Brown worships her from a distance -- a long distance. The few times he gets up the nerve to approach her, something gets in the way and messes things up. Usually, that something is Charlie Brown.

A lot of guys can sympathize, some more than others. For chronically shy guys, every girl is that little red-haired girl. And unlike the comics, it's no laughing matter. While we can't cure shyness in five easy lessons, we can give you five tips for overcoming your inner Charlie Brown -- five strategies to boost your confidence.


To start our classic plot of boy meets girl, we ask: How does boy meet girl?

5: Look for Like-minded Mates

Man and woman in movie theater
If you both like movies, go to a theater -- you'll have something to talk about after the show.

Having common interests or shared circumstances makes it easier to break the ice, and you're more likely to pick events that you'll both enjoy. Is there a classmate who loves Civil War history as much as you do? A coworker whose spread in "Farmville" is even bigger than yours? There's your cue.

If you're not a member of a group or club, consider joining one. Unless it's a fantasy football league or something similar, you'll probably meet a fair number of females. If you get to see each other in ordinary situations, that might be even better. When you clean cages at the animal shelter with someone, worrying about impressing her on a date seems kind of pointless.


Which brings us to the next tip: where to go and what to do.

4: Stay Within Your Comfort Zone

Man and woman at a diner
If you're not comfortable at loud clubs, go somewhere the two of you can talk.

Until you gain more confidence in yourself and the relationship, look for situations where you know your way around. That doesn't mean you have to go to the same restaurant every time. Just don't go to a grill-your-own steakhouse if you're clueless about cooking.

Pick an informal, open-ended event with no set agenda, like a street fair. If you and she "click," suggest a more intimate but nonthreatening follow-up: coffee at a popular restaurant, say, rather than a walk in a quiet park.


On the other hand, stay open to ideas that stretch a little beyond the tried and true. Trust your date not to suggest something where you'd really feel lost or bored -- she wants to have a good time, too!

Speaking of which, our next point explains how to feel more comfortable in any situation.

3: Prepare (but Don't Rehearse)

Man and woman sitting and laughing
Don't overprepare -- and it's fine to be spontaneous, too.

Take reasonable steps to avoid any surprises. Scout the place out and do a run-through. Find out how much money you'll need for food, tickets or souvenirs.

It also helps to have a backup plan. Check with your date first, however. You may think the auto show is a fine Plan B if you can't score tickets to the art exhibit -- your date, not so much.


After that, loosen up. Don't script the whole date. Think of the best times you've had with your friends. Did you have a program of planned events with predetermined starting and ending times? Unless you're thinking back to your sixth birthday party, probably not.

Unfortunately, the saying about the best laid schemes of mice and men is true -- for men, at least. Our next tip helps you deal with that possibility.

2: Don't Expect Perfection

Man and woman laughing
Don't try to be someone else.

Suppose you're enjoying a really good hamburger. Would you lose your appetite because you think it could use more onions? It's the same with dating. You can both have a good time even if your haircut looks nerdy and you don't get her jokes.

But suppose the burger is burned beyond edibility. Do you mope over the charred beef or chow down the tasty fries? Likewise, getting lost on your way to a destination could be a humiliating disaster ("I'm so sorry! I guess you never want to see me again") -- or a chance to show grace under pressure ("We missed the start of the movie. But I hear there's a cool show at the planetarium …"). The choice is yours.


Our final tip is the make-or-break factor. It's the aim that underlies all the others.

1: Make It About Her

Man and woman with remote control
Don't be afraid to ask her questions.

If you've been reading between the lines, you see this is the essence of a good date. Smile when you see her. Compliment her hair. If it's raining, offer to drop her off at the door.

Ask her questions; listen to her answers. It flatters her and takes the focus off you. But don't make her feel like a "CSI: Miami" suspect. Try comments that encourage a response without demanding one: "It sounds like you really like your job," or "I can't wait for winter to end."


When it's your turn, avoid making yourself sound like a superhero. When you're with guys, bragging is almost expected; to women it's a turn-off. A little modesty makes you look a lot better.