Your Call: How Do I Know When It’s Time for “The Talk”?

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We 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 on the letter below by leaving your advice in the comments section. 

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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 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.


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4 Comments on "Your Call: How Do I Know When It’s Time for “The Talk”?"

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The above advice makes sense but sounds like gaming. I personally couldn’t wait to see if he contacts me after I withdraw..sounds like he’s already being flakey, unless something else is up that has nothing to do with you. Maybe he is busy. But we always have time for the stuff that matters, don’t we. At least we have the time to call and say we are busy again tonight but we can’t wait to hang out soon. Or we forget to confirm the other person when we should because we have been bachelors for too long. You can demand… Read more »

I concur with misspiggy as well. If he’s not interested in contacting you after you give him tons of space, then you can figure out that he’s just not that interested any more.

Though if all of his relationships more or less expire after six months, I think you have your answer there as well. I would start weaning myself off this guy, honestly.


I think misspiggy is right. I’ll only add that it sounds like the situation is making you unhappy more than it makes you happy. While you’re giving him some space, you should consider what it is that will truly make you happiest and do that. Creating that happiness may be hard but you gotta look at the long road. Good luck and don’t give up hope on the good guys! They are out there 🙂

People can be a bit funny when they know someone else wants more from them (which I’m sure is clear to him at the moment). It can make them retreat, or view the other person negatively. But I wouldn’t want to wait another two months silently transmitting my feelings at him and him silently fending them off. If I were you I would spend a couple of weeks not initiating any contact at all. If he gets in touch and asks what’s up, I’d say airily, ‘Oh yes, I’m so busy at the moment, and it seemed like an opportunity… Read more »