Dear Dr. Ronn:

For over 3 years I’ve had a close friendship with a guy at my job.  At work he has become my “unofficial supervisor” (he doesn’t have a license so he really can’t supervise me).  I’ve been attracted to him the whole time.  We also spend lots of time together away from work, at my family functions and various other activities.  After all this time, I believe I must let him know my feelings for him.  How do I do it without seeming desperate?  Or, how do I push aside my romantic feelings and just maintain our great friendship?  Three years is too long to be interested in the same person and see nothing come of it! – C.I.*

Dear CI:

First, let me say that I truly believe that the best dates, mates and spouses were great friends first.  And, God knows, I’m NOT for women acting like tongue-tied little girls, who can’t speak up for themselves.

So, do I recommend that you pull your co-worker aside and tell him you’d love to upgrade from friendship to romance?

Absolutely not!  Unless and until he raises the issue himself.  Why?

When it comes to romance, men have been conditioned to be the “initiators.”  Like it or not, our cultural norms are:

MEN ask women for their phone number.  THEY ask women out.  THEY ask for exclusivity.  THEY ask you to marry them.

Doing those things makes him feel “correct”—i.e. strong, masculine, responsible.  So, when you do it instead, that dynamic abruptly shifts in a way that psychologically throws men off.

And, when men get thrown off, they tend to flee from whatever—or whomever—triggered that feeling.  Not the result you want, right?

But, you are dying to know if he feels the same way you do.  Basically, there are only three possibilities you could hear from him…

(A.) “YES, I’m romantically attracted to you.” The good news, you’ve got a match!  Two friends who want to become a couple.  The bad news: He felt that way and wasn’t willing or able to disclose it, until YOU set the stage.

Are you really looking for a man whose timidity paralyzes him from TAKING ACTION to express his true feelings?  If you tell him first you’ll make it clear that you take responsibility to do the “heavy lifting” in your relationship (so that he doesn’t have to).  Get ready, you’ll be the one who has to do it forever.

(B.) “NO, I’m not feeling you like that.” The good news: The facts are in, the mystery is solved.  You’ve still got a great friendship and that unanswered question no longer keeps you up at night.  Right?  Wrong!  The bad news: Both of you are likely to feel very awkward around each other.  You may feel embarrassed (and somewhat rejected too) around him.  You’ll now constantly wonder if he is interpreting your words, your tone, or behaviors as flirty, or even desperate.  He may feel self-conscious too: men are MOST uncomfortable when they feel they made a woman feel pain instead of pleasure.  They tend to withdraw from people and places that stir up their feelings of guilt and failure.

(C.) “Hmmm…I’m not really sure…” (Note: Anything other than a YES, should be interpreted as a NO.)

FACT: If a man is sufficiently attracted to you AND ready to for pursuit, he will let it be known and you’ll get to confirm your own feelings.   Since your friend has not brought that news to you, he is either not attracted or he’s not ready.  Period.

Here’s a simple, effective way for you to influence him to express his romantic feelings for you (IF they exist):


  1. Inform your friend that you have a new high-priority commitment to focus on your dating life.
  2. Ask him to become your “expert advisor” helping you in the dating process, by giving qualified feedback about men (particularly the ones you’ll be going out with).
  3. Explain that you’re going to have much less time to hang out together, because you need to invest more into your love life.
  4. Proceed to do EXACTLY what you said in Steps 1-3.

*Caution: Do NOT use this as a trick to manipulate him into declaring romantic interest in you.  It will ONLY be effective if you really mean everything you are telling him and you intend to follow through with it.)

If he DOES have romantic feelings for you, inviting him to help you in dating other guys will not be a desirable option to him.  He’ll soon respond (IF he’s courageous and communicative) by requesting an immediate upgrade from friends to boyfriend/girlfriend status.

Why?  Because you gracefully opened the door for him to either speak up or miss out—without him feeling you’re pressuring him or feeling you’re begging.

However, if he DOES NOT declare his romantic intentions (clearly, with actual words) he’s either not interested or he lacks the courage to say that he is.  Either way you deserve better.  In that case you’d only have yourself to blame if you stick around hoping and waiting indefinitely.

Obviously, if he outright tells you he’s happy just being friends, you’re wasting your time pretending there’s romance.  You must seek that elsewhere—NOW!

Remember, whatever you feed and water is the ONLY thing that will grow.  If you just want a life-long friend, then keep investing your primetime where you are.  But, if you sincerely desire a soulmate/husband you’ll need to put your best time, attention and effort into that.  Pick one.

*Questions posted here are edited for clarity and privacy.



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