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Ask Aslinn: Should I Ask Him Out?

Dear Aslinn –

There is a guy I like (as more than a friend) and I want to go out with him. How do I take it to the next level?  Should I ask him out on a date?

Sincerely, Interested

Dear Interested,

Ahhh yes… the ‘ole “I like you more than a friend” routine.  Welcome to the age-old question(s).  How do I let him know?  Should I let him know?  When? What? Where? If?  ahhh!  Welcome to humanity — this question has tumbled around the best of minds.

To this question I issue one challenge:

Become his best friend.

I know I know… I’m stepping on dangerous territory.  Every movie teaches, “don’t be in the friend zone.”  And maybe that’d be true if you’re looking for a 1 night stand (not recommended, fyi) — but if you are thinking long-term relationship — guess what?

 You end up marrying your best friend.

Definition of “best friend” = you…

  • … enjoy spending time together
  • … bring out the best in each other
  • … have grace for shortcomings (while gently challenging them to change areas that need to change)
  • … openly share your goals and dreams (and hopefully many of them compliment each other)
  • … know how to communicate clearly and effectively with each other
  • … practice forgiveness

Definition of “best friend” DOES NOT =

  • An asexual being who belches, spits, and scratches your “self” along with the rest of your “pals”.  (Yikes.  That’s terrifying.)
  • Asking him who he likes or has a crush on (you asking him implies that you aren’t an option.)
  • Attempting to control every area of his life
  • Insisting on being #1 to him; getting jealous over his other friends and relationships

You should become the person that he wants to call to tell the good news he just found out. He should discover that you are the one he prefers to spend time with because life is more enjoyable when you are there.  You listen to his dreams.  You encourage him in what he is good at.  Challenge him in areas where it’s possible [dare I say it?] he may be wrong.  This kind of close friendship is the breeding ground for love.  Obviously attraction is a big part as well, so if that last ingredient is there – he will definitely see you in a “more than friend” way.

If your friendship isn’t to this point yet, perhaps consider giving it some more time.  Maybe the foundation isn’t quite there to take it to the next level.

Should you ask him out on a date?  To that I simply say — be certain in your decision. Once you cross that bridge, there’s no return.  There’s no getting those words back. (There’s been many situations where my mind was screaming “COME BACK” to the words that had just left my mouth.  It’s NOT a good feeling.)  If he doesn’t feel the same, you may be ending what relationship does currently exist.  Some want to take that risk.  Others don’t.

I tend to lean toward letting the guy pursue.  That’s not to say that we don’t have our “ways” to help them along in that pursuit.  (Making them think they are pursuing you when you are nudging them in the right direction.)  We lady-folk are great influencers.  But that’s a post for another day…