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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


Join The Conversation
Totally-in-LOVE Totally-in-LOVE 8 years
Ive NEVER EVER went out with any one but i really think im in love but, i dont think he likes me!!! At first he would always flirt with me and my bff but he asked out my bff!!!! and they broke up 1 or 2 months ago. and he talks to me but doesnt really flirt with me. Should I ask him out???
ninjastarlett ninjastarlett 10 years
Well, she's right in one respect... with those kinds of responses, it makes your question sound kinda silly, doesn't it? You shouldn't be worried about how you might come off... if anything, being uncertain about it is a turn-off for guys. If you're worried about looking aggressive or easy, just play it casual. For instance, you could very casually say "I'm not usually this upfront, but would you maybe like to get some coffee some time?" Good luck!
lickety-split lickety-split 10 years
i would never have asked a guy out when i was single. but i have to say, the suggestions by ejean were very good. even i could do those. keeping it lite and fun is a great idea. in retrospect why NOT ask the guy out? what's the worst thing that can happen, he'll say no; boo-freakin-hoo. life goes on and you're free to day dream about someone else :)
madhatter madhatter 10 years
Even with my boyfriend, when I want to do something other than sit and watch movies or go out for dinner, I mention some concert or movie I want to go to, citing reviews or burnings CDs to garner some enthusiasm. The third tactic can be iffy though - I know there's some movie where the girl has two tickets, and her crush and his little cousin (brother? nephew???) end up using the tickets. Just make sure there's some sort of WE thrown around, not "I have two tickets."
kayleigh83 kayleigh83 10 years
I love this, any one of these would be my preferred tactic of showing a guy I was interested and wanted to take it to the next level!! I love it!!
tokenguy tokenguy 10 years
@Junebrug "Men "like" to be asked out because it strokes their ego" And it doesn't stroke the ego of a woman, to be asked out? It sure does for the women I've spoken to about this! "Men are very vain and they won't ask if they think they're going to get a no." Uhh, that's vain? How about, "Men are human, no one likes rejection so of course they're not going to ask if they think they'll get a no."
lilxmissxmolly lilxmissxmolly 10 years
i havent read the other comments yet (im about too) but nowadays women can ask men out...why do we have to wait around for men? why should we let them have that power? whats holding you back? All of those ways are great, but men are sometimes lazy or even just as frightened as we are-so why not take the initiative?
nessabum nessabum 10 years
um...i wouldn't follow that advice. i remember me and my guy. he wasn't going to say anything, and i got fed up with waiting so i said it. i wanted it enough to go backwards on my slight-old-fashioned-idea that he should be the one. but i told him instead. and guess what? i'm in a blissful relationship. be honest. don't beat around the bush.
junebrug junebrug 10 years
I agree with E. Jean and some other posters. Men "like" to be asked out because it strokes their ego -- the thing is, most of the time they say no, younger ones at least, older men may appreciate it. Men don't like to be put on the spot, they like to ask themselves. While they may think you're cool and want to be your friend, they often feel emasculated by women who do "their job" for them. It's ridiculous I know. Men are very vain and they won't ask if they think they're going to get a no. His job is to ask, your job is to be constantly dropping subtle and not-so-subtle hints that you'll say yes. If he still doesn't ask you out, there's a problem. Either he's not that into you, or he's into you but can't ask (personal problems, girlfriend, etc.) All you can do is send as clear a signal that you're interested as you can and leave it at that.
robinm999 robinm999 10 years
Read the book "He's just not that into you" and see if you still want to ask him. It's short, it'll go quickly.
kendalheart kendalheart 10 years
I think it's pretty great. I do agree though, not asking the guy out. If indeed he is interested in you, he WILL make that move, promise!
lizajane lizajane 10 years
I've often found that a simple, "We should go out sometime.." works great.. It is plenty to let him know that you're interested, without putting yourself too far out of your comfort zone. If he's interested, he'll take you up on the offer.. Another way is to figure out your common interests and build on that.. ie: I love live music, and so I often befriend people by telling them about a great new band I saw and suggesting we go check them out together.. The same can go for a variety of interests.. Good luck!
pud3333 pud3333 10 years
Holy crap! All those techniques are just so sneeky and confusing. As a guy, trust me, that only confuses us. All you're liable to give off are mixed signals, because let's face it,we're not smart enough to decypher them. We're pretty simple creatures. Just be straightforward. The pressure is always on us to ask a girl out. I know I would totally appreciate a girl asking me for once.
PrissyLilBadAss PrissyLilBadAss 10 years
This was a big, fat joke right? If not, I so don't agree with this advice. We ALL have to do things at some point that are out of our comfort zone! Trying something new is a very rewarding experience. Take a chance, you might surprise yourself!
amiemoos amiemoos 10 years
I think the advice is great! Number 1 has worked for only just recently :D
partysugar partysugar 10 years
E.Jean I love you! Everything you say is hysterical. Will you please be my therapist?
summer-roberts summer-roberts 10 years
What is wrong with asking him to join you and your friends (guys and girls) for drinks/bowling/ movies whatever. If he does, you can get to know him better without being on a 'date'. It lets him know you like his company. He then has the opportunity to ask you out if he want to.
martini-queenie martini-queenie 10 years
I’m aware this will come across as old fashioned, but I think the “just ask him out!” advice is a bit naïve. Men do like to be asked out, but they’re not like “what an empowered woman! she's not bound by social rules of conduct!” They like it because a) they like the ego boost b) they don’t have to make any effort to get you if they want to. Traditionally men are put in the vulnerable position of putting themselves out there while women are granted the authority to accept or deny. I think E Jean’s is good advice because it will give him the green light to ask her out without much fear of rejection, but not put her in a position where she looks desperate.
geebers geebers 10 years
I dont think this is bad advice because it depends on the person. If you are the type of girl that is confident and has no issue asking guys out -then so be it. Her point is to do what makes you you. Sometimes you need to step out of that comfort zone though - I feel like #2 and #3 ARE asking him kind of not sure how this is considered not asking out directly. I find #3 TOO direct.
julie090583 julie090583 10 years
It's been my experience that guys like the chase. But that doesn't mean you can't get the ball rolling. The key is to signify to him that you're interested while still letting him think that he has to work for you (like by doing the things E Jean suggested, though not quite so dramatically). Just be yourself but maybe a little more flirty. I'm sure some girls will say guys LOVE to be asked out and blah, blah, blah, but I can tell you that it's never worked for me to chase someone. If he likes me, he asks me out. If not, there's usually a reason. Good luck!
BethS BethS 10 years
Ugh. That was awful. Just ask him out. Guys really like being asked out, and even if they're not interested, they are super flattered, it's nothing to be embarassed about. Last guy that I asked out said no, but he was totally impressed and we still hang out as friends, and it will make it that much easier for me the next time I want to ask a guy out! Just do it once, you'll see that it's not that hard after all, and a little bit empowering :) You should have had LeninaCrowne answer this question, I like what she has to say!
fab4 fab4 10 years
Don't listen to E. Jean. Ask him out if you want to. Sometimes stepping out of your comfort zone is good. ASK HIM OUT. PS- I agree with LeninaCrowne. This is the worst advice I've read.
onesong onesong 10 years
lol - i like this. i think it's interesting, though, that it's okay for a girl asking a guy out to be "not her style," but what would we say about a boy who expressed the same sentiments? i'm not criticizing..asking a guy out is certainly not my style...i just find it interesting that that's okay. food for thought! that said, i agree here, and i'd go with number one. if you're especially nervous, do it with a group of friends first!
nicachica nicachica 10 years
lol...she's just being facetious and overly melodramatic to make some good ways to "subtly" ask him out without "asking him out. "Quick translation: 1. Bonnie and Clyde = Let him know you're on your way to X place and would he like to join? If not, no harm, no foul cuz you were going to go there anyway! 2. Amy Winehouse = I don't see how this is very different from No. 1 but it just seems like it compliments him and then insists on taking him for a drink/coffee/etc. Seems to be for the more upfront gals... 3. Green Day = Of course, this is yet another variation of No. 1 but its just saying "hey, i already have tickets to X and my friend just bailed on me. want to go?"
LeninaCrowne LeninaCrowne 10 years
some of the worst advice i have ever read. tactic #2 just sounds like you're desperate. "he’s a legend . . . he’s a genius . . . he’s an idol . . . he’s a god" what the hell? men should not be put on a pedestal and worshipped as "gods". there is no need to suck up to a man in order to get a date. if you do have to resort to such degrading measures you should be asking yourself if that's really the kind of man you want to go out with. if youre interested in someone and they seem interested in you and youre both unattatched, just ASK HIM. the worst thing he could say is no.
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