Asking a Guy Out

Now, a reader’s question:

Question: Any advice for a woman who is considering asking a guy out. I know him socially but not personally.

Answer: I think that’s great! A lot of guys find it refreshing for a girl to make the first move, and it’s also flattering (read: sexy) for a guy to know that a girl is interested in him. A few tips:

Do a little reconnaissance to confirm that he’s single. You mentioned that you know him socially, but not personally. Do you have any friends in common? Are you following each other on Facebook or Twitter? Contact a friend or check out his profile page to make sure that he’s not in a relationship.

Once you know he’s single, send out a casual e-mail/text to invite him out for a drink. I prefer meeting for drinks since it keeps your options open. Meeting for drinks is by its nature less formal than dinner, but if drinks go well, one of you can suggest dinner afterward. Likewise, if the conversation over drinks isn’t flowing easily (beyond the usual first date jitters), then you can end the night after a drink or two.

There are people who think of coffee as an ideal first date activity, but I feel as though that’s too casual and trite. A coffee date could come across as though you aren’t genuinely interested in him. If you enjoy similar hobbies or a shared love of sports, then you can always pitch an activity or watching a game instead of drinks.

If your interaction with this guy tends to be more in person, then you can ask him out for a drink during normal conversation. Whether virtually or in real life, keep your tone light and use phrases that are comfortable for you. You can broach the topic in a general way, leaving it up to him to pick a time and place by saying:

What are you up to this weekend?; or

I never feel like we have enough time to talk/I’d love to talk with you more about [insert relevant subject here]. We should grab drinks sometime.

Or, you can be direct and pick a place and a day that works for you like this:

I’ve heard good things about this wine bar/brewery/lounge, and was thinking of checking it out on Thursday. Wanna join me?

What you say or how much of the asking you do depends on your style, preference and comfort level. I make sure a guy knows that I’m interested, but I ultimately let him decide when and where and do the asking.

In my opinion, if you pick the time and place to meet, then you should pay for drinks.

Readers, do you agree with me on this? What other suggestions do you have for this girl?

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