How Do You Approach a Woman for a Date?

We all have social anxiety to some degree, but some people have an easier time walking up to total strangers and striking up a conversation. For others, the fear of rejection is so strong it prevents them from even saying hello to someone who catches their eye.

So what can you do about dating if you tend to be shy in social situations?

It’s not easy. But thanks to online dating, some of the initial barriers to conversation have been removed. Chatting with someone online can is easier than chatting with them in person – mostly because you have a little time to think about responses (and delete!), putting your most charming self forward from the start.

But if you find yourself at a bar, on a hike, or at Starbucks and someone you find attractive walks by, instead of looking down at your phone, it's good to muster the courage to say hello. There are a few things to keep in mind when you don't know how to approach someone in person.

Practice makes perfect. Don’t assume that you have to walk away with a phone number or else you’ve failed. The win is in the small steps taken and the effort made. If you have terrible anxiety about approaching a woman, try to strike up a conversation without a goal in mind. And if she isn’t interested? Just try again. Not everyone is going to be open, and you’re not going to be Casanova right off the bat. Give it time, and allow yourself to practice.

Don’t open with a pick-up line. Instead of putting this kind of pressure on yourself to “impress” her with your cheeky confidence, try instead to be more authentic. Compliment her on something unexpected (not her body or curves – but the details like her sense of style, or even her laugh). Aim to make her smile, not to get her number. If she thinks you’re just looking at her as a “score” you’ve already stopped the conversation.

Take your mask off. When you are genuinely being yourself, people connect with you because you are most confident as your true self, according to dating coach AJ Harbinger. If you are wearing the mask you think you should be wearing, then it’s harder for people to trust you. When it comes to connecting with women, they need to feel secure. They need to feel like they can trust what you say before they open themselves up to you. Be yourself.

Make her feel safe. Women like to flirt, but they don’t like to feel like prey. Instead of coming across as aggressive or overly flirtatious, try asking questions and getting a feel for who she is and what she likes. If you don’t know if you should try a line, then don’t! Instead, take a classy approach to allow her to trust you. Trust is the most important thing to gain before you can truly attract a woman. As dating coach Julie Spira advises, offer to pay for valet parking rather than just drinks. This will earn points, because you are showing her that you view her as a person, not as a conquest.