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You Asked: I Need Dating Advice!

Dear Sugar,

Last year I met this guy who is pretty much my ideal man. He's funny, sweet, athletic, smart — I could go on and on. Anyway, we met at work and he was my supervisor for a while. We no longer work together, but I see him quite often. Needless to say, I developed quite a crush on him; however, I have no idea if he knows this or even how he feels about me. From the things he says to me, my friends think the feeling is mutual, but I’m not sure because he’s always so sweet to everyone and therefore what he’s saying to me might not be the special something they seem to think it is. I’d like to drop the hint that I have a crush on him and see how he responds, but I’m not sure how to go about doing this. Both of us are pretty shy, so I don’t think I could just come right out and tell him without scaring him off or making a complete fool of myself. Would it seem immature and high-schoolish of me to ask one of my friends to drop the hint? — Scared to Be Daring Dara

To see DearSugar's answer

Dear Scared to Be Daring Dara,

The only way you'll ever know if this guy feels the same way about you is by putting out your feelers. Sure, exposing yourself can be very scary, so if you'd feel more comfortable having your friend drop a hint, go for it! Why not? To avoid sounding immature, make sure she uses tact and ask her to make her hint very subtle.

Once she's done her part, you're going to have to step up and do your part too. Going a little out of your comfort zone can be incredibly rewarding, so flirt with him! Give him the interested vibe without being too pushy. Remember, guys can be very insecure, and sometimes the fear of rejection can be too crippling to even take a chance, so if your crush senses that you have feelings for him, chances are he'll step out of his box too. Good luck!


Join The Conversation
Trixie6 Trixie6 9 years
How much do you know about him? Key into something that you know he likes (foreign movies, sports, live music, comedy clubs) and invite him to go with you.
mlen mlen 9 years
would it be totally out of character to do a happy hour? i'd gather a few friends from work- not a large group but maybe like 2 or 3 others and just be like hey we are gonna go grab a drink or gonna go grab some dinner friday after work- want to join? see if he comes out and see how he acts outside a work setting. if he can't come though at least he'll see you invited him and maybe he'll suggest alternate plans
hotstuff hotstuff 9 years
"In those days, women were all housewives and those "men" used to beat them up! So lets get over the oldschool style." What the hell kind of days are you thinking about? Real men have the courage to ask a woman out that he's interested in!
happiness80 happiness80 9 years
@ hotstuff: "What happened to the days when men were MEN and had the balls to man-up and ask a woman out?" In those days, women were all housewives and those "men" used to beat them up! So lets get over the oldschool style. I think there is nothing wrong with a woman making the first move. The should look to take the lead afterwards though.
CaterpillarGirl CaterpillarGirl 9 years
just ask him, dont say "i have a crush on you" thats very 7th grade. ask him out, if he says no, than there you go.
flyinglimegreen flyinglimegreen 9 years
Yeah, I agree with not emailing him the article. That will TOTALLY freak a guy out, especially if he's already kinda shy. And if that's not something you would normally do, he might get the wrong opinion of you and be turned off for the wrong reasons. Do you have any mutual co-worker friends. I always find it easier to kinda poke around that region. Say, if you have a friend who's close to one of his friends. You could definitely try to get some info that way. Mutual friends are the BEST. If they see a potential match, they're always trying to help it along. And also if they see some wrong info, they'll immediately set the record straight. That's usually the least confrontational. This way, if he's not interested, neither of you will feel awkward because it never really came up...right?
bengalspice bengalspice 9 years
I say bite the bullet and drop a hint. It can even be as some subtle flirting. Or maybe an impromptu dinner/drink plan. You should sit down and have some one-on-one time to talk and flirt a little without friends and coworkers as distractions in the background. Then drop your hint that you've had a crush on him for a while, dropping a compliment wouldn't hurt either. He might be really flattered by your honesty.
lizzie_ttu lizzie_ttu 9 years
I have to disagree with petite. Sorry! No offense! I think e-mailing an article to him with a note will totally freak him out. I do agree with hotstuff in the sense that if he's interested, or "just that into you," he'd make whatever necessary efforts to get to know you outside of work. I also like greentea's advice & I think it would be OK to say, "Hey, my friends and I are stopping by (whatever bar) after work for some drinks. You should stop by!" If he does, then he's definitely interested in hanging out with you outside a work setting. If he doesn't, then you'll know and you at least put yourself out there and can figure out whether to keep making efforts, or not.
petite42 petite42 9 years
... if you want to find the article, it was picked up widely by the press, based on research in the Journal of Psychological Science. Go to Google News and type in "Men Really are Clueless" and you will find the article.
petite42 petite42 9 years
There was a recent news article - I think it was in Science - about a research study that suggests that men really are clueless when it comes to women's signals. It was quite interesting. According to the study, men will either misjudge a women's friendliness as being a sexual come-on when it's not; OR they will totally miss that she's making a sexual come-on and think she's just being friendly. Men, apparently, just aren't as good at reading such cues. What I suggest you do, is find this article, and email it to him with a note, something along the lines of, "In case this applies to you, just wanted to let you know that I really AM flirting with you... in my own shy way." Or something like that. If you're too shy to do even that, then perhaps just sending the article to him, and asking him for his opinion and experiences, will get a conversation going. I would NOT ask a friend to talk to him for you. Not only is that juvenile, you run the risk that your friend will end up having an "in" with him. Don't you remember junior high school at all??? It was always the friend that had her own vested interest that would offer playing Cyrano!
Shopaholichunny Shopaholichunny 9 years
I don't think it's immature. I do this for my girlfriends and vice versa. :P But, if you really like him why don't you make the move? If both of you are shy then nothing might happen at all and then you might be wondering what could have happened in the future if you don't do anything about your feelings.
hotstuff hotstuff 9 years
What happened to the days when men were MEN and had the balls to man-up and ask a woman out? I personally think a man who's interested will show you he's interested, and ask you out without having a friend do it like he's in freaking 1st grade, but I guess no harm would be done in following DS advice!
Greentea1203 Greentea1203 9 years
I went through/am still going through this with a guy at my work! While I always thought I was shy, he is SUPER shy! I came to the conclusion that I would have to be the 'aggressive' one and ask him out. (luckily for me, he was the one to ask me out first) Just ask him if he wants to hang out sometime! The worst he can do is say no, and trust me, you'll get over it. This guy and I are still in that 'hey, do you want to hang out?' phase and I still get nervous when I text him and ask him that question, fearing rejection, but I figure every time he texts me the same question, he has the same fear, or whatever, so just go for it!
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