Dear Reverend,
I am pretty shy and slightly socially awkward. I want to start dating, but I’m really struggling to flirt and get across to other people that I’m interested. There is a very cute person who works at a store that I go to a lot. I haven’t been able to talk to them because I am so anxious and it feels weird to try to flirt with someone doing their job. It’s already hard enough to flirt as a shy person, and I don’t want to overstep.
Emma Coy (woman, 35)
Dear Emma Coy,
As a formerly shy person, I can tell you that the motto “Fake it ’til you make it” did wonders for me. Although it’s important to be yourself, it’s OK to adopt a confident persona to help dip your toes into the social scene.
When you’re getting ready to go out into the world, think of getting dressed as putting on your confidence armor. Wear clothes that make you feel great. Do something snazzy with your hair. Putting a little extra effort into your outward appearance can be an easy confidence booster.
As far as flirting with someone when they’re working, it depends on the situation. It’s easier to strike up a conversation with an employee at a bookstore than a cashier in a busy checkout line. You have to read the room.
If you frequent this person’s place of work, they are probably already familiar with you. It could help with your anxiety if you don’t think of it as flirting. Just talk to them like you would anybody. Make eye contact. Introduce yourself and ask their name. Don’t linger too long; a little bit goes a long way, and if your interest is reciprocated, you can build on your conversations with each visit.
If things are going well, try dropping them a casual invite to an event. For example: “There’s a great band playing at Radio Bean on Saturday. You should come.” If that feels too forward, you could always put an I Spy in this paper. When it’s in print, tell them that you think they got spied. If they didn’t see it already, I can guarantee they’ll look for it.
Good luck and God bless,
The Reverend
This article appears in The Québec Issue.
