The Poor Man’s Way To Get To Date 2: Shhh

Dating 101: Dating Tips for Shy Men. Duet Right!

  1. Even if she asks you out, you pay the first go. Whether it’s a coffee date (in this case my “date” ordered “a hot chocolate with whip cream”—raised eyebrow) or a 5-star restaurant. Hint: if you’re not sure it actually is a date, in my book—the man pays. (Smart choice: don’t choose a 5-star.) And what if she has a single friend who you might totally dig? You’ll forever be known as the cheapskate. Antiquated, anti-feministic, unfair. All true. But, hey, you have a penis. High five!
  2. Be sure you want to spend $4.50 on a fancy coffee for this gal! If you think it’s a waste of your hard-earned dollars, then skip it (and her) and keep on keeping on—and move on. If you think she might be cool, even if not your forever lover, make the investment. You might learn something new about women. Or yourself. Be curious.
  3. Drop the skepticism. Yes, all of us who’ve suffered through a bad date (or several) feel jaded to some degree. Unfortunately, jaded isn’t sexy. Try open-mindedness and, for Jebus sake, don’t talk with venom about all the bad experiences you’ve had. If you must get your point across, be playful and fun. Instead of “all the girls I’ve met don’t look anything like the photos they post,” say, “I’m so glad you look as great as your photos!” (Grin/chuckle/wink) Or instead of “all the women I’ve dated are just into money,” say, “You seem like a woman who appreciates more than just the finer things in life …”
  4. When on a (first) date in a café/restaurant, do sit facing the crowd, not each other. This avoids awkward silences with a people-watching distraction. (Thank you, Matthew Hussey, for this tip!) Or, at a bar, try to sit beside each other at the corner where you can both watch the behind-the-sushi-bar action. (Thank you, A, for a great choice of seating!)
  5. Don’t talk endlessly without giving your date a chance to participate, especially if all your talking causes you both to miss the live show you’d planned on attending. (I was easygoing about it, but your next date might not be!) Yes, if you like her, you’re probably nervous. Take a deep breath then … tuck (your tongue in), drop (the chatter), and roll (the convo back to her).

Dating 101: Dating Tips For Shy Men is from my own in-the-field dating with “real” men experiences and recent feedback from random women I impulsively interview.

If you have a dating or relationship question, please send me an email or ask in the comments below.

Remember, I’m not a shrink. I’m a single, dating chick—master dater! Even better.

xo Wingmam

p.s. I could really use your help with something…spreading the word, namely my words!

About the Author Anna Jorgensen

Vancouver Dating Coach for Shy Guys & Introverted Men. Matchmaker Liaison. Founder: Wingmam

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