HOW TO ASK SOMEONE OUT ON A DATE. AKA, HOW TO DO THE DIRTY DEED. IN CASE YOU NEVER GOT THE MEMO, HERE'S SOME SPECIFIC ADVICE ON HOW TO ASK SOMEONE OUT ON A DATE.
I don't know how to date. People often say things like, “I was married for 10 years. Now, I’m divorced & single and don’t know how to date. I don’t know what to do.”
Not. We all really know what to do and how we expect to be treated. Use your head. Don’t make excuses for yourself or your date. Children know how to plan for a date: they know how to pick up the phone, call someone they like, and invite them out on a date.
Take a moment to make a plan for at least 2 to 3 days in advance. Like meeting for drinks at a nice wine bar. Beforehand, read our deal breakers and dating advice.
Practice/roll-play with a friend. Or, record yourself using the voice memo feature on your smartphone. Play it back and listen. If it sounds stilted, keep practicing. If you blow it, take a mulligan. You may be surprised at how you sound, just like many contestants on Idol appear to be. If your voice is too high (this happens with nerves), breathe from your abdomen, not your shoulders, and lower your voice. We expect even George Clooney rehearses his lines. Master your approach.
Take a deep breath and slowly exhale. Pick up the phone. Do not request dates via texting. In this scenario, George is calling Angelina. Introduce yourself and ask if this is a good time to speak (i.e. "Hi! This is George. Is this a good time to talk?). If she is free, make a little small talk. Ask "How is your day going?" Listen to what she says. Use good manners, be polite & pay attention.
Then, gently, cut to the chase. Say, for example, "I was wondering if you might be available this Thursday to meet for a glass of wine?" If you don't drink alcohol, order mineral water.
If Angelina is busy, ask "When would be a better date & time?"
If Angelina is rude & says something like, "When hell freezes over!" and blows you off, just be nice. Take the high road and say, "No worries. Take care" and hang up the phone. Drop it and move on.
If Thursday works, set a specific time and place to meet. For instance, "Great! Let's meet at The Wine Bar in Palo Alto on Ramona Street at 7pm." Be specific so that there is no miscommunication.
If Angelina says, "Oh, I broke up with my last bf, Brad, there..." you could say "Angelina, then that's a perfect place to get back on the horse!"
Alternatively, say, "Where would you prefer to meet, Angelina?" If she says, "I can't think of anything." Suggest a backup plan. "Let's meet at The Cask on Laurel in San Carlos at 7."
What if you get voice mail? Don't freak out. Relax and leave a nice message. Say "Hi! This is George. We were introduced through PreQualified Mates (Explain how you know Angelina. A lot of active people are busy and meet many people and may not recall who you are or how you know each other).
For instance, "I was wondering if you would like to meet for a glass of wine this Thursday? Please call me back at (your phone number) to let me know if that works and we will finalize the details. Hope to hear from you soon!"