First Try

Dear Miss Lonely Hearts,

How do I take step one? This may sound silly, but how do I even begin to ask someone out? I've never dated anyone before or anything like that, so I genuinely wouldn't know how to ask without it sounding uncomfortably awkward. Even if the person isn't interested, I'd rather still just be friends, and I'm worried that if I mess up asking them out that it'll ruin this nice dynamic we currently have!

First Try


Dear First Try,

There’s no concrete formula for asking someone out (I would lament this lack but, fortunately for
me, it means I still have a column to write). Everyone approaches it differently—chatting someone
up at a bar, sending bad pick-up lines on Tinder, passing a folded-up piece of notebook paper reading, “Will you go out with me? Check yes or no,” a phone number scrawled on a coffee cup—the list goes on. However, since you’re not some sleazy dude at a bar, a third-grader, or a barista (I’m guessing here...that one is possible), your best bet is to just shoot your shot. If you don’t want to make a grand gesture on your first try ( flowers, pizza with M&Ms spelling out “date me?”), keep it simple and be authentically you.

Assuming that you talk to this person regularly, the next time you see them, ask them what they’re doing tomorrow night or over the weekend. If they’re free, there’s your opportunity! Suggest doing something together, just the two of you. Because you’re already friends with this person, you have a leg up in the game: you know their likes and dislikes, so you won’t ask them to go see a band they hate or suggest getting coffee when they really prefer tea. If you’re able, suggest going somewhere off campus—it can be somewhere as close as the Rhododendron Gardens, but it’s always nice to get to know someone better when you’re outside of the Reed bubble. If not, keep it low-key and hang out on the Great Lawn after grabbing ice-cream sandwiches from Commons. Maybe even take a walk in the Canyon! And most importantly, make sure they know that it’s a date. Tell them that you’re interested in being more than friends. You can even tell them that you’ve been crushing on them for a while. It may sound dorky to you, but trust me, they will be flattered above all else!

If asking them out point blank still seems too daunting, give the old middle-school-dance routine
a try: ask a mutual friend to feel out the situation for you and see if they would be interested in going on a date with you. If so, you’re in! But, no matter how you choose to ask them out, let them know that there will be no hard feelings should they say no, and if they turn you down, it’s okay. It’s always worth a shot.

And, First Try? Don’t sweat it too much. If you sound awkward, that’s okay. As your friend, they’ll be forgiving, and, as a potential partner, they might even find it endearing! Go easy on yourself.

Wishing you luck,
Miss Lonely Hearts