Expert: Susan Dunn, Dating Coach - 11/20/2007

Question
Hi!  I'm in My mid thirties, divorced for several years now with 3 kids.   There is a man (my age) that I fancy quite a bit.  His son goes to the same school as 2 of my children, as a result I see him every day when picking up my kids.  Here is the problem.  He is without a doubt very very shy.  I think he likes me too(so my gut tells me)...but I cannot be absolutely certain.  I have noticed he comes at the same time, parks near me every day he comes(if I arrive first). He'll wait in his car to exit his car once I arrive and walk at the same time as me if he arrives before me.  I will catch him looking at me from further away but once he gets closer he looks at nothing but the ground!  I have tried to walk closer to him in hopes to spark a conversation to no avail.  He will only allow me to come so close before almost running away. Seriously!  He starts speeding up!  

I have never seen a woman pick up his son, he wears no wedding ring, I suspect he is a single dad.  

I would like to talk to him.  I would like to find out if he is single for starters.  The fact that he is so extremely shy is making me nervous!  

He doesn't talk to anyone at the schoolyard at all.  Otherwise, I would have tried to approach one of his friends. (It's not unusual for parents to talk with each other waiting for the bell)

I don't want to look like a fool!  So far I have not made myself overtly obvious.  He may have noticed I have tried to approach him, but he may not be sure, because I backed off almost immediately.  

The only reason I noticed him in the first place was because I sensed he liked me.  Then I took a closer look at who was looking at me all the time and realized I liked him too.

I feel like an idiot because this shouldn't be that complicated.  If I was younger with no kids this would be much easier.  I am worried he may think I am married because I share custody and sometimes my ex goes to pick up the kids or we even go together.  (we remain friends for the sake of the kids)  But my ex and I walk far apart and associate with different people on the schoolyard, and quite a few of the parents are aware that we are divorced.

How can I tactfully approach all of this?  It's been going on for 2 1/2 months.  

Answer
Dear June,

Well, there's nothing wrong with striking up a conversation ... but if he won't let you get near him, there's something wrong.  If he gets within range, tryin a friendly conversation.  Otherwise, I would let it go.  If he did like you, that's rather peculiar behavior.  He would find out if you were single, he would strike up a conversation ... it would all be easy to do in that situation.  I would pay attention to the fact that his shyness makes you nervous, and that you know it doesn't have to be that complicated. Not good signs.

Warm regards,
Susan Dunn
www.susandunn.cc
sdunn@susandunn.cc