Should You Ask Him Out First?

Relationships |

Ask a guy out first – and you run the risk of “Winning the Battle but Losing the War.”

Making the first move

I can’t tell you how many single friends have asked for an opinion on this one.  It usually spawns from liking a guy, knowing the feeling is mutual, yet he hasn’t initiated asking her out.  So the question arises – “Should I just ask him out?”

My answer:

“No. Do not ask him out.  And btw, don’t ever ask a guy out first. I will Unfriend you.” 

I jest. That usually gets a laugh. I’m not one to mince words and if asked I will give it to you straight!  No waffling or sugar-coating, just a straight, simple answer.  The next question is “Well why not?”  Ugh… Ok, ever heard the saying “Win the battle, but lose the war”?  That’s why.

If a guy likes you, he will make the first move. If you make the first move, you run the risk of winning the battle but losing the war.  In other words— it may result in a first date, a relationship or even marriage if that’s your end-game, but at a fundamental level, guys like to feel that they pursued and won you over. That there was a competition and he prevailed. 

When you are the first initiator and the pursuer, you relinquish your power. The power dynamic changes from you as the decision maker and one-to-be-won, to him, as the one-to-be-won.

When the relationship goes through trying times, and believe me—it will, you want him to remember what a challenge it was to win you over. Guys place a subconscious higher value on something they had to “fight for,” vs something that was pretty much there for the taking. I know this sounds super annoying to some, but IMO—that is just the way it is.

But I think he’s too shy to ask me out?!

Nope.  My answer still stands.  If you think he’s too shy or feels super intimidated by your awesomeness – the solution is simple:  Smile, be kind and receptive when he talks to you—basic things to make him feel comfortable.

A shyer type will probably dip his foot in the water by saying something like “we should see a movie sometime.” Instead of saying, “Great! How about Saturday?” Instead, just smile and say “I’d love that!” 

Or maybe he says, “Have you been to that new sushi-bar downtown?”  Instead of saying “Not yet – want to go?” Say “I haven’t but I’d really love to go!”  I mean, c’mon – the gate couldn’t be open any wider.  Now he knows you are interested. Ball is in his court. Leave it alone – let him pick it up.

I know it’s not the 50’s – but trust me on this one!!

Believe me—I KNOW this sounds really, really archaic and it’s not 1950!! This is especially cringe-worthy for those of us with very strong personalities, who have no problem asking for and going for what we want professionally and in our normal day-to-day lives.

But what serves us professionally, and in the general day-to-day world, isn’t always what works best for us long- term, with guys and relationships. 

Not ALL tradition is bad.  There are some things that work to our advantage, and this is one of them.  In allowing him to initiate, pursue and win you over – you are actually quietly creating more value in his eyes.  

Why?  Because you aren’t easy pickings, asking him out, pursuing, paying the tab, etc.  I’m not saying that it’s right or even accurate.  It’s just what happens – IMO of course. 😉

What do you think?  Share your feedback below!

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