Should I ask him out, or wait for a while and see what happens?

There is this guy that I’m in band with that I like and I’m pretty nervous that he doesn’t like me back. He told me that he liked this one girl that has a boyfriend, but he isn’t interested in her anymore. The other night he walked me home and held my hand the entire time and gave me a really long hug. When he pulled away his face was really close to mine. I never wanted to kiss someone more than I wanted to kiss him at that moment.

Music play / Do what the music say.

06-13-23-28-43 / 06

Hello Diner. If nothing else, you, your love interest, and the gentleman who sent in this Order show that letting the fear of failure stop you gets you a lot of frustration and very little chance of kissing. Much less, at least, than speaking up—or actually going ahead and planting a kiss.

There is a comforting certainty to chance. People forget that. They assume chance inevitably summons disappointment—like sunset: twilight, or humidity: frizzy hair. But that simply cannot be true. If you set things in motion, if you move your piece, if you pick a card any card, if you observe the quantum wave function, Fortune—despite her undeserved reputation for being flaky—promises you two things: 1) a response and 2) the assurance that the response can be a good one. Not may. Can. She delivers those guarantees unfailingly. She has been every femtosecond for 14 billion years now. Nothing in this universe or outside of it has delivered so perfectly consistent. You just have to do your part and play.

Diner, you live in a culture of isolation—where something as human and visceral as touch is guarded and controlled with courtesy and etiquette. Holding hands is so intimate that the gesture generally implies a silent acknowledgement that the two people want more than friendship. Think about a scenario where you would hold hands with someone you’re not interested in. First off, you wouldn’t. Secondly, even if you did for whatever reason, you’d feel obligated to explain to the person: just friends—and even then, you would still be concerned that you may be sending your friend mixed messages. Holding hands is just that intimate in your culture.

Since there was no caveat from your love interest, chances are he wants a little more than friendship. If you look at all the possible outcomes of your asking him out, at worst he’ll feel flattered and turn you down. Best case scenario, you two have a lasting relationship. Somewhere in the middle of that spectrum, you two date, but find out that you’re not suited for each other. Hopefully the two of you won’t take it personally because that’s just how dating goes. If you’re fine with each of those outcomes, then there really is no downside to asking him out—with the upsides being kissing, romance, and sex. Definitely not bad at all.

Virgil wrote in his epic The Aeneid, “audentis Fortuna iuvat,” Lady Fortune favors the bold. [1] That phrase has been on family crests, war banners, emblems, and skin for generations because of its simple truth. If you are brave enough to seek the future you want, Fortune necessarily has to deliver outcomes where things go right. Even without the gift of foresight, Diner, this humble Fortune Cookie sees more good outcomes than bad for your situation. In this case, the odds do seem to be in your favor. Just play. Good luck, Diner.


[1] Virgil (c. 29 - 19, BCE). P. VERGILI MARONIS AENEIDOS LIBER DECIMVS. Retrieved September 26, 2014 from