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Ask E. Jean for DearSugar: Should I Ask him Out?

Dear E. Jean--

Being somewhat of a traditionalist, I have never asked a man out for a date. However, currently there’s someone I’m very interested in dating, who acts as if he is interested in me, but he hasn't made the move. I am willing to go out of my comfort zone and take a risk here and ask him out, but what kind of message will that send? I don't want to come off too aggressive or easy for that matter, but I don't want to let a good guy go! So what do you think? Should I ask him out?

To see E. Jean's answer,

MY YOUNG TROLLYMOG: No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. You should not “ask him out.” Lord!

I’m breaking into a persp. just reading your question. There would be no blunder so abominable, no goof so gauche. Why? Not because you’re worried you’ll “come off too aggressive or easy.” But because you’re worried you’ll come off as too aggressive and easy. It’s simply not your style. It is, as you say, “out of your comfort zone.”

So here are three ways to ask him out . . . without asking him out:


You’ll just . . . assume he’s aching to go out with you, be with you, worship you.

IE: The next time you see him, you’ll smile, work the lashes, slip your arm through his and say, “Oh, I’ve got such a thing for a hot basket of French fries . . . . sneak away with me! Let’s run off to--” [and here you’ll whisper such a posh/evil sports bar, pool hall, dive, the very name will conjure up most dangerously attractive place in the world.]

It’s not about asking the guy on a date--it’s about suggesting he tag along on an


You’ll just . . . compel him to follow you to the ends of the earth.

IE: This is a slight variation on #1. When next you’re conversing with the lad, rivet your attention on him--he’s a legend . . . he’s a genius . . . he’s an idol . . . he’s a god-- and say, “you’re so brilliant, you deserve a Mojito (Guinness, Caffe Americano )” pluck him by the sleeve and simply whip him (Gwen-Christina-Avril-Scarlett-Amy style) to the closest pub, coffee shop, outdoor café.


You’ll just . . . inflame him.

IE: When you see him, you’ll smile, and without saying a word, you’ll hold up two
tickets to the Green Day concert.

Then he has to say: “Gawdam! You got Tickets! Are you kidding? Wait--wait--are you kidding? Can I go? You mean--dang!--I get to go with you?”

Good luck, darling! Let us know how it goes!

To see more advice from E. Jean visit Elle Magazine and


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