Dear E. Jean: I’m 29 years old, and I still have no clue how to convey to a man that I’m interested in him. (Unsurprisingly, I’ve only ever had one real boyfriend.) I hold him to high standards when it comes to demonstrating his interest in me, yet my own attempts to reciprocate—like hitting the like button on Facebook—are so understated that they’re practically invisible.
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How can I improve at this? There’s a new guy I’d like to start dating. I want him to be my boyfriend. I’m not unintelligent. I understand what needs to be done. I just can’t bring myself to do it. Friends have given me the perfect lines to say, but when the moment arrives, I shrink back. I completely freeze!
I’ve already been intimate with this guy several times, so what kind of signal does he need from me to understand that I’m into him—yes, for the physical side, but also for something more? I’ve lost some great potential partners to women who are far more forward. So my real dilemma is, How do I express interest without looking like an idiot? —Stumped
Stumped, My Lovely Little Churro: Bah. If you want to succeed in love, you have to be ready to look ridiculous. Send him this message: “Snacks. Thursday. 8:30 Balthazar. It’s a date.”
With just seven words, you’ll have made three things perfectly clear:
- You’re into him.
- You’re hoping he feels the same.
- You’re proposing an official outing.
[Readers who’ve been fuming with indignation since finishing the last paragraph of your letter may now return to their usual polish and composure.]
P.S.: Of course, Miss Stumped, you wouldn’t have to make the first move if our ridiculous hookup culture hadn’t invented “backward dating”—first you sleep together, then you go out—a fun idea when you want to get wild in the garden like a bridesmaid on a tear, but not great if you’re seeking a sweet (or dark, eh?) romance.
Nor, I suspect, would you need to send this text if we weren’t living in Tinderland. Now, I enjoy Tinder. I endorse Tinder. Heck, I’m on Tinder myself. Tinder is awful, wonderful, clever, foolish. But because Tinder makes these super-fast hookups possible, after we’ve hooked up, to shield ourselves from rejection, we switch off the alluring, innate, man-conquering courtship signals that Mother Nature spent 3 billion years perfecting—we turn them off, I say, just in case the guy doesn’t like us as much as we like him, because we don’t want, as you put it, to look “like an idiot.”
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And so where does that leave us? [Cover your ears, readers. Auntie Eeee is about to start swearing.] It leaves us with you having to fucking text the fucking moron and bluntly tell him, Dude! Let’s date! Damn!
As Miss Jane Austen says: This is fucking insane! Or, uh, I believe the exact quote is: “We can all begin freely—a slight preference is natural enough; but there are very few of us who have heart enough to be really in love without encouragement.”
This letter is from the E. Jean archive.






