Dating Tips

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7 Expert Tips for Asking Someone Out Online

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Asking someone out on a date is one of the more stressful actions of human existence. It is a pride-swallowing, anxiety-producing, stomach-churning act that most black singles will struggle through at one time or another.


Below are seven tips for making this unpleasant, rocky experience a little bit smoother.

1. Speak loud, speak proud


OK, obviously you’re not speaking loud verbally via email, but it is just as important to be straightforward and unambiguous. There’s nothing worse than asking someone out and wondering if the request was somehow lost in translation. (Do they know it’s a date? Or do they think it’s a friend thing? Damn. I bet they’re gonna bring their kid sister.)

2. Use humor


Funny people get action. There’s no WAY Arsenio Hall could have landed “Forever Your Girl”-era Paula Abdul without throwing out a few gut-busters. Reportedly, he made her laugh so hard she peed her pants.

3. Don’t be a jerk if they say NO


If they give a patently ridiculous excuse, just accept it. Don’t pry apart their “logic” or bombard the person with questions. A person is rarely better disposed to one who points out their idiocy anyway. On the other hand, accepting rejection with dignity may lead them to question why they turned you down; being a jerk just confirms the initial reaction.

4. NO does NOT mean YES


Don’t keep asking, emailing, annoying. Please. It’s embarrassing for them and pathetic for you. If they change their mind, you’ll be the first to know.

5. Suggest a specific thing at a specific time


When asking for an online date, don’t just say “do you want to do SOMETHING, SOMETIME?” Have a plan. Make it fun. Define when and where. Otherwise, “sometime” can easily turn into never.

6. Offer YOUR phone number, so they feel secure


Offering your phone number allows a prospective date to contact you when they feel comfortable and secure. This goes double if your prospect is a woman.

7. Be prepared to fail.


There is no way you’re going to win the game if you don’t take the field. Sure, there will be some 90 mph fastballs and unhittable curves. But hang in there long enough and you’ll get a pitch worth swinging at.

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