A woman covering her face with her hands

Pickup Lines for the Painfully Shy

by Jeannie Assimos - December 12, 2012

Just because you’re painfully shy doesn’t mean you’re destined to loner-dom at friends’ parties or social events. To many, shyness is an endearing quality.

Here are a few not-too-painful pickup lines for shy people:

1. Keep it simple and direct. Smile and introduce yourself.

2. Recruit a wingman/wingwoman. Have friends casually introduce you to their single friends at parties.

3. Give a specific compliment. If you’re in line with a cute stranger and you like her hat, say so. Small talk about winter headwear might lead into an opportunity to ask her out.

4. Ask for a recommendation. If you’re at a holiday party, ask the single gal next to you if she’d recommend the mixed drink she’s sipping. Everyone enjoys being an expert.

5. Comment on the surroundings. “I feel totally overdressed for this event. I always fall for the ‘formal’ in the ‘semi-formal’ dress code.”

6. If there’s music, ask him/her to dance.

7. If a cute stranger holds the door open for you, offers a helping hand or pays you a compliment, thank him/her — with an accompanying smile and intentional eye contact.

8. Find something you can bond over. If you’re a dog lover, head to the dog park where you might meet someone equally passionate about canine friends. If the cute co-worker is wearing a shirt from your favorite band’s latest tour, strike up a conversation about your (obviously) great tastes in music.

9. Acknowledge your shyness. “Hi. I don’t know anyone here and I’m horrible at meeting people. Can we pretend we’re friends so I don’t feel so awkward?”

10. If you’re too shy to use pickup lines, use that to your advantage. (No one likes them anyway.) “I wish I could get away with using hilarious and endearing pickup lines, but I always screw them up. So, hi. My name is______.”