Q: Okay, so here's the dealio: I've know this guy, we'll call him Shawn (because that's his name), almost 20 years.  Our parents are friends and it's not unusual for me to stop by my parents house and find Shawn chatting with my family.  Out of the many years we've known each other I've spent a fair few of them intensely curious about dating him.  Lately it's gotten more so, I kinda stopped caring about "what would happen if it didn't work out" since our families are buds, I just want to know if it'd work out. Life's short right? So, in an empowered woman moment I asked him to dinner, it seemed relatively date-like, but I'm not sure he fully got the gist that that's where I was going with it.  Gender roles have gotten so confusing and I don't know what I should do, what's too much, or how to maintain the "delicate" lady-like role (I mean, I don't want to be fully in charge of the dating relationship, ya know?) while trying to break through his thick man skull.  What's a girl to do? How do I make this happen? Suggestions?


One (Thick-Headed): I once found myself on the flipside of a similar situation. A couple of years post-graduation, a school pal moved to my hometown. Our mutual friends were scattered across the globe, so it seemed the most natural thing in the world to hang out just the two of us, over lunch or dinner. He was smart and witty and charming, and we shared tons of super esoteric interests and experiences. Conversation flowed easily and always left me smiling. But I was totally blindsided when he confessed to feeling more than friendship. Things got awkward and we stopped spending time together. I was bummed, because I genuinely enjoyed his company. But, who's to say, maybe a clean break was better for him. You need to ask yourself which worst case scenario is more unbearable: your existing friendship exploding into awkward nothingness, or your heart and dignity being subjected to the slow burn of unrequited love. Once you know, you'll know whether to play it cool or play with fire. If it's the latter, I say spell it out in English plain enough that not even the thickest-skulled caveman could misunderstand. As long as you maintain a ladylike smile, I don't think you need to worry about further jumbling post-traditional dating gender roles. Good luck!

Two (Indecision 2012!): I didn't fall in love until I started dating my husband because one of three pieces were always absent: It wasn't the right time, the right place or the right person.  Before you jump into this, I would recommend you consider those three things.  I know two women very well who have done this -- asked boys straight out about what their relationship was or wasn't or why they had never had a romantic relationship with a given boy.  One ended with assurance the relationship was NOT going to be romantic (ouch) and the other one is engaged to the boy she asked.  What made the difference? Who knows.  But I do know that the 2nd friend and her friend were a little older than the first pair and that they knew one another REALLY well.  They knew that there was a good chance it was the right person -- both had a vested interest in seeing whether things would work because they already knew that they cared about one another a great deal.  It was the right time in their lives -- they both were looking to find someone to settle down with and had lived enough of life that they wanted to find someone to live it with on a more permanent basis.  Finally, they were in the right place -- professionally, geographically, emotionally.  Ask yourself if those three pieces are present, say a little prayer, then do as you see fit.   

Three (Harsh Realist): How do you make this happen? Um, don't do anything else. 

I really appreciate your bold move in asking him out, but if he was secretly pining for you he would have taken advantage of your alone time and made it clear that you were cruising on a two-way street of love. And correct me if I'm wrong, but it sounds like that didn't happen at all. I know this sounds harsh, but in the words of a guy I know "men are only 'thick-sculled' when it comes to women they're not interested in." Ouch, I know, but he has a point. In my humble opinion, it's not worth the emotional trauma of chasing after him and having to face rejection head on. Especially if you'll continue seeing him around all the time. So, be proud of yourself, and take that strong lady-power places it'll be appreciated!

Four (Impressed): Oooh! The passion, the thrill--the intrigue! I find this to be very exciting. Clearly you're pretty balsy--which is cool. Aaanyway, I think a lot of elements factor into whether your presumptive paramour thinks your evening was an actual date. First, do you usually hang out together? Alone? For dinner? Did you dress up? Did he dress up? Who paid? You may want to ask some of these questions and--depending on the answers--reevaluate the situation. Regardless, you can always write him a quick note explaining how much you enjoyed your evening with him, and suggesting something else you two could do together. Depending on his response, you'll probably be able to see where you stand a little better. No matter what happens, congratulations on being an empowered woman! Sometimes I like to pretend that I'm one, too. After reading this, I'm not sure I would qualify...

Five (Highly Paid Analyst*): Awwwww dude, that sounds weird. For an insight into the Male Mind, I'll refer you to two sources: a previous lady-asks-guy-on-date Ask 5 (graciously answered by some of our favorite gentlemen), found here, and my very own psyche. It is possible that this man, much like myself, always finds a decidedly non-romantic interpretation of others' blatantly romantic gestures towards him. I can easily see how this obtuse boy could morph 'hot dinner date with strong, independent woman who don't play by no arcane "gender rules"' into 'friendly catch-up over a meal with old family buddy', because I've done similar things myself. It is also possible that this guy is a yeller-bellied-lily-livered coyote, put off by your strong, confident ladyhood (a.k.a. he's just not into you).

I think that you can choose either painful or disappointingPainful: tell him plainly that you think he's neat. But say it like this -- "I romantically like you". As unromantic, indelicate, and potentially humiliating as this option is, it totally disallows any misunderstanding. Either he thinks you're super keen too, you get married, and have lots of fat babies,** or you end up avoiding each other's awkwardness at family BBQs for the next few months. Disappointing: let it go. Ignore the dude, release any notions of your amorous future together, and find another mister with whom to have lots of fat babies.** Or you could just listen to one of my sisters. Yeah. Do that.

*Full disclosure: I have absolutely no idea what I'm talking about.
**Assuming you want fat babies. Svelte babies are also an option, as well as no babies at all. Whatever you're into.

Have a question? Ask 5You'll have a 1 in 5 chance that 
someone will see it your way!
Just send your questions to: