Q: I know a really nice, handsome, smart, (single!) guy. We're good friends, but I really, really like him. I'm a little in love (and have been for awhile). I think he likes me too, and mutual acquaintances agree. My problem is this: he hasn't asked me out, and I'm starting to get impatient. Would it be a turn-off if I do the asking? I know that some forward thinking, non-lesbian feminists have OKed it, but is it really appropriate for the lady to make the first move? Will it make me look desperate?

The ladies of FIVE felt sadly unequipped to answer this question, seeing that they, too, have repeatedly pondered this perplexing puzzlement without resolution. They have consequently entrusted this week's Ask 5 to a quintet of knowledgeable parties. Namely: men.

Mr. One (Republican): I really shouldn't answer on the grounds that my traditionalist notions will incriminate me.  I can say, however, that, particularly in matters romantical, One (my better half) is a master at hinting rather than asking.  Such intimation is a skill at which the fairer sex enjoys a considerable comparative advantage, stereotypically speaking.  That said, most males (extrapolating from myself) are pretty tin-eared when it comes to absorbing and responding to hints, so if you actually want your message to get through, your intimations might need to involve neon lights, painfully obvious puns, or groping.

The Future Mr. Two (Better Late?)Like most men, I was never particularly good at picking up on signals.  To this day, it is still not my strength, but it has taken me many years to learn to think like a woman.  

For example, a woman may mention to a man that she likes a certain type of flower or restaurant or piece of jewelry and then may repeat that statement several times over the course of weeks or months.  To men, this may seem to be just a casual observation of a particular aesthetic or taste.  But NO!  A woman would never say something like this lightly.  What she really means is, "I like that flower [or restaurant or piece of jewelry], and if you're worth anything, you should buy it for me".  

We often wish for things to be S-P-E-L-L-E-D  O-U-T.  

However, in spite of our protestations, men are often attracted to a woman's complexity.

My advice - respond to him, drop hints when possible, but keep it discreet.  If all else fails, smack him across the face and tell him you like him.

Dr. P. (Chief Love Physician)Many nice, handsome, smart & single (or, you know, formerly single, but now in a long term relationship with a blogger...) guys perpetually exist in the dreaded "friend zone" with girls and don't know how to escape. He might really like you but assumes that you are 1) too good for him, 2) not interested, 3) Completely unaware of his affection for you.  Also he might never have asked a girl out before.  Nice & smart, does not a Romeo make.  So if you're pretty sure that you aren't reading too much into the situation and have existed in this friend vs. love-interest disequilibrium for at least 2 months, then I'd say go for it!  Both of you are likely to breathe a sigh of relief and it will give you the freedom to take off from there. Also later on in the relationship, when handsome & smart never has time to spend with family and friends, can rarely take you on dates, has no money and poor immediate job prospects, please constantly remind yourself how nice, handsome and smart he is...

Astroboy (5's Resident Don Juan): The dating world can be rough for a guy.  Tradition and social norms have put most of the pressure on him.  The embarrassment of rejection can be absolutely terrifying, especially with the added stakes of damaging a great friendship.  While not absolving the guy of his responsibilities completely, I find it can be refreshing and very flattering when a girl makes the first move.  Not only is it a huge confidence booster, but it saves us the uncomfortable experience of the 30-45 min where we try to practice what to say with our thumb hovering over the dial button to ask the girl out.  I wouldn't worry about coming off as desperate (unless you showed up at his house with a marching band and a plane towing a banner, that might be a little much).  Overall, I think he would be flattered that such a great girl liked him enough to make a move herself.  He'll feel wanted instead of always trying to convince the girl he's worth a shot.  If asking him out on a straightforward date seems a little bold, try an indirect approach.  You could ask him to help you with a project around the house (rearrange some furniture, some simple handyman repairs, teach you how to do some simple maintenance on your car, etc) and make him dinner afterwards as a thank you.  Even though you are technically making the first move, the project gives you a perfect excuse and he'll feel manly helping out pretty a girl.  This will give you some quality alone time together and an opportunity for some playful flirting.  Don't be afraid to be what you may think is a little obvious. We can be pretty thickheaded sometimes and too worried about impressing the girl to pick up on her subtle signals.  If he doesn't figure it out and beat you to it, let him know that you had fun and would like to do something together again.

Brother Z (Fourteen Years Old): Basically, guys are pretty nice. If a girl came up and asked me out, I would say yes, even if she was not "all that". Worse case scenario -- you take her on a cheap first date and don't call her back. Nobody likes being rejected. it really sucks. If you're worried about being told off, try coming onto him a little stronger, like grab his tush as you walk by or comment lewdly on his appearance and stare at his junk. Mmm, if that doesn't work...He's probably more interested in me than you. On a slightly less flippant note, if a guy is mean enough to not even take you on a first date (circumstances permitting), he is probably a putz. If it doesn't work out, I'm single and tall for my age.

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