How to Ask a Lady on a Friend Date

I had spoken to her a few times at work. She was super pretty, wore the coolest clothes, and always seemed to be laughing.

“I like her,” I thought, and then, because my brain often gets stuck on Baptist, “Not LIKE HER-like her...just, you know, she seems cool. And I want her to be my friend.” But I felt a little weird. I clearly had some sort of friend-crush, but had no idea how to act on it. Do I “ask her out”? Do I start casually dropping by her desk to chat? Do I surprise her on work IM one day with a random question?

Well, it seems she had the answer all along: SHE ladied up and asked me on a friend date, in the coolest, most casual way possible, and I was like, “DUH, you’re an idiot, TNR. This is not that complicated.”

And indeed, it’s not. One thing I’ve learned over the years from people like my friend above and from experience is that, when it comes to people and making friends, it’s simply just not that complicated...and if it IS complicated, it’s probably due to weird pre-conceived notions about giving people the “wrong idea” (since when is it a bad thing to ask someone to join you for a drink? I don’t usually want to bone every person I have a beer with, and if I did, I wouldn’t be able to walk most times). Look, I get that there are “social norms” but I also get that it’s not so hard to just be YOU and if people want to be all like, “I think she LIKES ME likes me” then meh. Maybe that friendship is not to be.

Anyway, without further ado, here’s a few simple, uncomplicated ways to ask that special lady or dude on a friend date.

The Conversation Approach

One girl I met in grad school and I just happened to figure out that we had CRAZY similar backgrounds (the whole Baptist girl gets married and divorced thing). Because we had that one thing in common, it was easy to say, “We should totally do breakfast this weekend. It’s hard to find people that truly understand what I went through!” Use anything in your conversation to suggest a friend date over drinks, food, or hell, even your favorite TV show.

The Direct Approach

This approach is how my work friend asked me on a lady-friend date. I think I had complimented her outfit or something and she was just like, “You seem cool. Wanna get drinks on Saturday?” And we did, and it was a blast, and it turned out that we had much more in common than I thought.

The Casual Approach (aka The Group Friend date, aka The Person Once Removed date)

One friend mentioned that her sister was into a lot of the same things I also enjoy. After seventy-two more conversations that went like this:

Me: “Oo, I totally love that!”

Her: “Holy crap and for the love of god, SO DOES MY SISTER.”

Me: “We should all get together sometime.”

Badda boom, badda bing, the next time my friend and her sister went out for drinks, I was invited along. And lo, it was the good times.

The Twitter Approach

Tweet, tweet! It so easy to sound non-creepy in 140 characters or less (unless you’re that one guy whom I’d never met who tweeted, “Baby, you’re beautiful! Where do you live?” Um, DELETED). I’ve actually set up several lunch friend/networking dates with all genders through Twitter. A quick DM, and there you are, ready to meet a potential new friend, and you didn’t even have to woo anyone beforehand!

How about you? Are you good at “picking up” people for friend dates? Or do you find it's awkward to turn a friend-crush into an actual friend?