How To Sidestep Shyness

by Sabrina Cohen

The dating world is already daunting. Add in shyness and increase the challenge factor. But all’s not lost: with effort, persistence, courage, and the below tips, even the most timid dater can overcome!


A good ol’ fashioned smile is easy to flash. It’s also pleasantly disarming. Smiles have a way of quieting insecurities for both of you—and upping the ante on confidence, friendliness, and fun. It’s also great to precede your smile by making (and holding) eye contact with someone you find attractive. Yes, stare—and use their gaze back as a doorway to connect.

Ask for directions

You’ve gotta be on your toes for this one. If you see someone you like, jump at the opportunity by asking for directions. Be a little proactive: figure out a nearby “faux” spot. Practicing on a regular basis can help you ease out of the shy zone. Spend some time walking around and stopping random people for directions. Warm up by starting with people you don’t want to date. Then move on to more challenging prospects. Remember: no risk, no reward.

Ask about a spot to eat

Go a step further by inquiring about something open-ended, like area eateries. Your question can spark conversation about the neighborhood, food preferences and beyond. Mention having time to kill (hint hint). If the person is interested, it can be your first date!

How do you overcome an attack of shyness? Share your approach below!

Sabrina Cohen is a blogger, copywriter, and creative consultant for



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Filed under Date Etiquette, Dating Tips

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