How to Get a Shy Woman to Initiate

Men's Dating

How to Get a Shy Woman to Initiate

Bethany Heinesh Bethany Heinesh • 9/25/14

There are a lot of women who struggle with being shy and wish they could be more outgoing. They find it almost impossible to do away with their perpetually bashful disposition, however, and often carry their shyness to the extreme.

For a man, I imagine this can be quite frustrating. Getting a woman to come out of her shell and interact with you can be very difficult, especially if she is naturally timid or introverted.

Not only does this make it challenging to get to know a woman you’re interested in, it can make for a very boring phone conversation or a completely one-sided discussion at dinner. Yes, going out with a woman who is relatively shy can make for one long date, not to mention a wary relationship.

The thing about shy women is that you have to know how to communicate with them. You must handle them with care and tread lightly — in word and in deed.

Naturally intimidated by new people and social situations, shy women withdraw in silence to keep their composure and to feel a sense of control. They act shy for fear of saying the wrong thing or acting socially inappropriate. They want to avoid awkwardness at all costs, so they cleverly eliminate the possibility of looking foolish by not saying anything at all.

Gain her trust.

Remember, though, that just because someone is shy at first doesn’t mean she’s not an undercover chatterbox. In today’s crazy world, women are overly cautious in the presence of strangers and rightfully so. In order to get a shy girl to let loose, you must first gain her trust.

Many women who initially seem shy will talk your head off once they feel comfortable around you. Treat her with respect and prove you are trustworthy, honest and sincere. In time, she will open up and let you in. Be patient.

If you happen to be falling for a woman who is a little on the shy side, take note of these profound insights and apply them accordingly. If you struggle with shyness, these will be helpful for you as well.


“One of the best ways to counteract shyness is to

center the time spent with your sweetheart on

an activity that doesn’t involve talking.”

1. Go slow.

If you are aware that your date is somewhat reserved, be patient. If you appear forceful or pushy, she will run like the wind.

2. Get back.

Physical boundaries are very important in the beginning of a relationship. Don’t put your arm around her or try to hold her hand unless you are absolutely sure these are welcomed gestures. Give her the space she needs to feel comfortable around you before you make a move to get a little closer.

3. Pass the sauce.

Take your shy little sweetheart to a gourmet dinner. Great food makes for a lighthearted conversation about one thing you both have in common — the meal you’re sharing. Plus, there isn’t room for uncomfortable silences when you dine as a duo because food creates a great distraction.

4. Be the man.

Take charge of the situation and show your girl you’re not afraid to be who you are. Be a gentleman and pull out her chair, open her doors and order for her. Pick up the tab and walk her to the door when your date is over. When a woman feels good to be in your company, she is more likely to talk openly with you.

5. Give her smiles.

A man should always be armed with an arsenal of jokes. Women love a man who makes them laugh. You wouldn’t believe how easy it is to break the ice with a joke and win her over with the punch line. Ask her to tell you a joke so she will feel encouraged to come out of her shy-induced stupor.

6. It’s your turn to chat.

When you’re out on a date with Shy Shelley, it’s your job to keep the conversation alive. Ask questions to get to know her better. Tell stories and entertain her with your goofy impression of David Letterman. Do whatever it takes to avoid a lull in the conversation. If you know your girl is shy, you should show up to your date ready with interesting things to talk about. Current events, politics and the weather always make good topics.

7. Go see some art.

One of the best ways to counteract shyness is to center the time spent with your sweetheart on an activity that doesn’t involve talking. Go to an adult arcade, put a puzzle together, see a movie, visit an art gallery or tour a museum. Being able to spend time with someone without the pressure to come up with witty and intelligent things to talk about is a beautiful thing.