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How to Convince a Shy Person to Be Your Valentine

Contributor
By eHow Contributing Writer
(6 Ratings)

Does she blush and look quickly away when your eyes meet across a crowded room? Does he mumble and stammer if you hint you'd like to join him for a cup of coffee? Shyness shouldn't be a stumbling block when you're seeking out a Valentine.

Difficulty: Moderate
Instructions

Things You'll Need:

    Breaking Through Her Shyness

  1. Step 1

    Smile - sincerely, not suggestively.

  2. Step 2

    Remember that women appreciate gentleness and quiet humor.

  3. Step 3

    Ask one of her friends for an introduction.

  4. Step 4

    Look for a mutual friend who can give you her telephone number.

  5. Step 5

    Ask to share her table during break or lunch hour. Mention Valentine's Day.

  6. Step 6

    Leave a message on her voicemail or home answering machine saying you enjoyed talking with her. Mention Valentine's Day again.

  7. Step 7

    Find another reason to meet her on neutral ground.

  8. Step 8

    Compliments, compliments, compliments - perhaps a bit of judicious flattery.

  9. Step 9

    Send her a Valentine's Day card several days before the celebration.

  10. Step 10

    Be specific when you ask her to celebrate Valentine's Day with you. Vagueness allows a shy person to find numerous excuses.

  11. Step 11

    Be simple with your plans. Dinner at an expensive restaurant and dancing at a trendy club may be too overwhelming.

  12. Step 12

    Consider a date the night before Valentine's Day or perhaps lunch on Valentine's Day so that she won't think you're being overly romantic too soon.

  13. Overcoming His Shyness

  14. Step 1

    Smile - and flirt just a little.

  15. Step 2

    Use lots of eye contact when you're in a group situation. If he makes a good point or agrees with a point made, look at him directly, smile and nod.

  16. Step 3

    Remember, a man who's shy can be approached more directly than a shy woman.

  17. Step 4

    Compliment him.

  18. Step 5

    Move "into his space" - stand close when talking, touch him lightly on the arm or hand, never let your eyes stray from his.

  19. Step 6

    Find common interests socially or professionally. Listen to his views.

  20. Step 7

    Mention Valentine's Day in the context of a general conversation.

  21. Step 8

    Leave a note on his voicemail or send him an e-mail. Mention Valentine's Day.

  22. Step 9

    Ask him to do something personal for you - ask him to carry your laptop and briefcase to your car, for example.

  23. Step 10

    Send him an electronic Valentine's Day card a few days before the celebration. Make it humorous, but personal.

  24. Step 11

    Get tickets to an activity he truly enjoys and ask him to accompany you.

  25. Step 12

    Be aware that he may not take the hint. It may be up to you to ask him on a Valentine's date.

Tips & Warnings
  • Pursuit of romance is acceptable. Pursuit after thorough rejection can be perceived as stalking. Stalking is criminal behavior.
  • Wait for the celebration to indulge in champagne. Meeting for a date with alcohol on your breath can be a quick turn-off.
  • Remember, it isn't all about looks.
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