Dating - When to Talk About the Serious Stuff?

[PlayingwithChance]

I've been dating/hanging out with this guy for about 3.5 weeks now. He leaves this town in about a month.

He's a first time dater, very nervous, very anxious, very shy, and doesn't take the initiative, so I've sort of had to do most of the work in trying to get him to come out of his shell. He usually goes along with it though, except any form of sex.

Anyways, how soon into the dating phase is it considered to be good practice to begin talking about... dun dun dun... FEELINGS.

You know, the whole "What do you think/feel about all of this, especially with you leaving soon and all?" or the "I know you're uncomfortable with the more intimate stuff... why are you so nervous? Is there something I can do to help you with that?" or the "How do you feel about this whole dating thing...? Is the pace okay, or do you need space?"

I'm not exactly sure WHAT to talk about, really. I guess what I want to achieve are the following:
a) Know how he feels about me
b) Know how he feels about US
c) Know where this is going, or where he wants it to go
d) Know how to approach the topic of sex (mainly oral, with me giving... as that's what I want to do...)
e) Know if he enjoys me always taking the initiative and asking him to hang out a lot
f) Let HIM know that I want him to show more affection and/or take the initiative more, let me know how he's feeling and what he's thinking more often

UGH. So complicated! Thanks for the help guys

 

[justsimon]

I talk about my feelings whenever I start to have them. There's no wrong time.

 

[PlayingwithChance]

Do you guys think that discussing feelings would scare off someone who's new to dating, not completely comfortable with being the recipient of affection, etc.?

 

[KaraBulut]

Do you guys think that discussing feelings would scare off someone who's new to dating, not completely comfortable with being the recipient of affection, etc.?

If I understand the situation- he's leaving soon? How can your scare off someone who is already going to be leaving?

And if not now to have that talk, then when?

This isn't about talking, though. This is about you risking rejection. And the question really is- Are you asking about his feelings before you take the risk and tell him yours?

 

[G-Lexington]

Tell him. Now.

Lex

 

[hanshansen]

Look, either you guys were meant to be together (the 'fundamentals' are right) or not. If the fundamentals are right, it is virtually impossible that talking about this stuff can screw things up for you. Maybe it won't go perfectly straight away, but you'll be able to work through any issues.

Conversely, if it does screw things up for you, you'll know the fundamentals weren't in place. Because it means this is not a person you can be honest with about serious matters.

So yes, talk. You can't lose.

That said, you can do it in different ways. You can be more or less 'heavy' about it, you can give them sneak previous of what you want to say and arrange a convenient time or spring it all on them at once just before they have a major work meeting, etc.

Just make that call. Like I said, if you were meant to be together, you'd have to make a pretty massive error of judgement for things to go wrong.

 

[PlayingwithChance]

Thanks guys for all the advice. We did talk, and it just didn't work out. I understand it though, he just wasn't that into me physically. I'm not really insulted or hurt, as I understand people have types and preferences, and so do I. It's not something that can be helped, or necessarily the fault of anyone.

Only thing I really feel is a tad disappointed things couldn't have worked out, cause I really liked this guy. But at the same time, it's quite a relief to have some form of definition to the whole dynamic between us, whether good, bad or final.

I'm hoping he and I can still be friends for the duration of his stay here, and that it won't be awkward or prove to be a tease to my psyche. I'll have to make that judgment in a few days or so.

Definitely though, I'm glad I got an answer sooner than later, because now I can finally, truly begin to let myself move on, rather than cling to false hope and expectations.

THANK YOU ALL!

 

[KaraBulut]

Definitely though, I'm glad I got an answer sooner than later, because now I can finally, truly begin to let myself move on, rather than cling to false hope and expectations.

Good for you for having clarity and moving on.