How Do You Know when It's Time for "The Talk"?

The TalkWe get a lot of advice questions coming in at EMandLO.com, but sadly, we just can't answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call by leaving your advice in the comments section below.

I have been single for several years. I am a divorced forty year old woman with an almost 18-year-old son. I've been divorced for 7 years and have only been in one serious relationship and have had 2 short lived "flings" and now this. I've been seeing a 30 year old guy (single, never married, no kids) for about 4 months now.


Firstly, I don't know how to date. Early on I freaked out because I was developing feelings and got scared and had a meltdown. We talked it out and I put all my feelings out there and since then I have just tried to be honest about how I feel. I haven't played the game of playing hard to get or any of that. If I want to see him or talk to him I contact him and tell him.

He is a very reserved guy and likes a lot of alone time to himself. For the most part I am good with that.We have talked about how I feel when I want to see him and he declines and he has told me that I should not take it personally because he works two jobs and he does require alone time and it has nothing to do with me.

But my feelings are deepening and I want to have "the talk" with him to see how he feels about me. Lately I feel like he is keeping me at a distance more than when we first started seeing each other. He used to initiate spending time with me more than he does now and I don't know what to do because it makes me feel sad and insecure about everything.

He previously had told me with his past relationships that at the 6 month point he figures he should know if the realtionship is going somewhere.(None for him have lasted more than six months since a 3 year high school relationship.)

My question is, do I have the talk with him now because my feelings will get hurt when he doesn't want to see me and I really just want to know where we are, or do I wait a couple of months and give him his space and see what happens? I don't want to scare him off, but I do want to know how he feels, because I know how I feel and I want to get closer to him...and get out of my head because I want to be with him and when he doesn't contact me for a day or two or declines seeing me if I ask to get together I get hurt and confused because I don't know how he really feels and I'm not sure what to do.

Like I said, I don't want to scare him off so I wonder if I should just hang in there and see what happens or just force the issue for better or worse so at least I know what's up. Help?!

-- Tongue-Tied

What should T.T. do? Let her know in the comments section below or join the discussion already in progress on EMandLO.com.