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Asking Someone Out: How Do I Do It?

A guy about to ask a girl out.

Howdy Joan,

I can talk to anyone, but the second it comes to getting it out there that I want a date, I don’t know what to do. How do I ask her out? I can do it when I online date, but asking someone out is a different situation when I’m out. 

A lot of guys get worried about laying it on the line and asking for a date, because this question does two things: 1. Reveals that the guy is indeed interested, and 2. Opens him up for a potential sting if she declines. If the thought of asking her out gives you a panic attack, remember what you’re actually doing: Reserving time with her to see if she can hold your interest.

When you believe the stakes are lower, you’ll feel more comfortable being yourself because you won’t have a stressful question looming in the back of your mind. After having a short and light conversation, you’ll be able to tell is there’s a preliminary connection.

Before you think about asking her out, spend some time coming up with a casual date idea. Don’t be that guy that asks, “So, what do you want to do” – you’ll come off as an amateur. Have a plan and make it a plan that’s easy for her to accept. Asking her to an all-day music festival is a big time commitment, but asking her to join you for a cocktail is a much easier commitment to accept.

When it comes to that date idea, keep it casual and light. Save that fancy dinner date for another time. If you’re ready to spend a ton of time and money on someone you don’t very well, you’ll seem overly anxious to please and cater, which comes off as desperate.

When you do get a yes, go ahead and get something on the calendar. Stop trying to continue the conversation—the date will give you the opportunity to learn more. The night before, shoot her a text with time and place, and you’ll be ready to rock.

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