Date?

[Pandys]

Sorry if this is a bit long, just trying to answer as many questions as I can up front.
A little while ago I posted an add on CL in the M4W section titled Feminine side the gist of which was; CD looking to talk meet or more. Fell free ask any questions.
I only got a couple serious reply's, one of which resulted in a meeting after several phone conversations and e-mails. We had coffee and talked for about 2 hours.

She is very attractive and we seem to get along great, however she is about 10 years younger than me.
I told her I was a closeted CD, but other than that not much of our discussions had anything to do with dressing.
I have been trying to figure out if she is interested in me as a "buddy" a BF or maybe something more.
I told her early on that there was no pressure in any way and that what ever she wanted "us" to be I was interested. The only response one way or the other was that she would be a friend as long as I wanted her to be.

Yesterday I asked her if she wanted to meet up (via e-mail) for coffee, shopping or something. She said "Shopping with you sounds fantastic. Please let me when and where"
My reply was, whatever she felt like depending on what she was looking to get.
She e-mails me Let's go shopping Sun @ 2.
I was thinking great a little Christmas shopping would be fun.

Then a couple minutes later another E-mail "I think Dawn needs to look pretty and sexy so we will go to **** mall?"

Now I am really confused I was starting to feel more like this would turn into a dating thing but now I am not so sure. I know I should just be patient and let things develop as they will, but it is tough.
It has been a long time since I have dated, and I had forgotten how hard this part is.
Advice, thoughts, insight?

Dawn

[Amberhea]

I think you should go as yourself first in male mode just to make sure she's interested in you as a person and not only as Dawn. Let her get to know Dawn throughout the relationship. Or you could simply ask her.

[Marcelle]

Dawn,

I agree you should be up front. Your original advertisement said "CD looking to talk, meet or more". It could very well be this gal took the ad as "meet and be friends" or she might want "more" and CDing is a bit of a turn on to her. If you are comfortable, I would meet her "en femme" then ask her outright if this is a "friendship" only or if there is a potential for more. Worse case scenario, you end up with a GG friend who enjoys allowing you to express your femme side in public (wing girl) best case scenario, you have the opportunity at a relationship with an understanding and supporting person.

Hugs

Isha

[sweetshauna]

I tend to agree with Isha.

[Pandys]

Dawn,

If you are comfortable, I would meet her "en femme" then ask her outright if this is a "friendship" only or if there is a potential for more.

I have never been out dressed and I don't usually under dress. Since we are going shopping for Dawn I am thinking about wearing my girl Jeans and panties.
I am going to call her later and hopefully find out a bit more.
When I told her I was OK with whatever she was looking for I did ask her to let me know that when she said she would be my friend. I am wondering if she has made up her mind to how far she wants this to go, so I don't want to push.
I agree it sounds like a win win for me, I just really want this to become romantic.

[jenni_xx]

Think you should turn up dressed in male clothing. If only because of her comment "I think Dawn needs to look pretty" - that sounds to me like she wants to work on your look. So let her!

In regards to your concern (the reason why you wrote your post), I can't help but think that she's interested only on a platonic basis. That's not to say it won't go further, just that the ball is in her court in that regard. So I think you'd be right to be patient and let things develop, but only on the understanding that "things" may not develop, and friendship may be the outcome from this particular person.

But that's not so bad right? I mean, you'd have at least made a friend, and that's a good thing in and of itself.

[samanthasolo]

If you do infact go out in public dressed it is a cool opportunity regardless of what her intrests are in you. Just the fact that she was implying that you show up dressed without any idea of how passable or blendable you are in public is pretty awesome. Have a conversation with her during the course of the shopping trip to clarrify exactly what both of you are hoping for in terms of your friendship and if at all there is the potential for more. She might be feeling a bit confused just as you are and it really is just a matter of getting in the same page with eachother so you remove any potential for misunderstanding, or expectations! Sounds like fun no matter what happens so enjoy it!

[suchacutie]

You told her you were closeted so if she understands that she wants to buy things for Dawn for you to model later. What happens then will be apart of the adventure.

[Pandys]

She knows I don't go out dressed, but maybe I should bring a few things in case we get to try stuff on later?

You told her you were closeted so if she understands that she wants to buy things for Dawn for you to model later. What happens then will be apart of the adventure.

I would like that.

[CarlaWestin]

I would view the genderist side of your personality as a component and not a main definer. You're off to a good start in the fact that she sounds, well, accepting. My radar would be going off a little that you might just be playing to her curiosity. I'd be very keen to ulterior motives this early on in the relationship. If you really need to satisfy her interest, you could start out by underdressing. That's naughty and scandalous enough from a newbie's point of view. I mean, come on, you need to have a good understanding of a person's history before you just open up to them. And that applies to everything else, not just CDing.

[Desirae]

I would go for it and just let whatever happens, happen naturally, and don't try pushing it. I think most successful relationships are ones that started out in friendship. Be her friend first. I think you'll know or sense if things seem like they should progress more. Even if they don't, you may end up with a very good friend out of the deal.

[Jenniferathome]

Here's a crazy idea... ask her what she means.

[Lorileah]

Interesting, so many here WANT a GG who will go with the dressing and when one finds one they ask "should I?" Really? I read the email as she wants to go shopping WITH Dawn. Your ad says you are a CD, you told her you CD, she is willing to be with Dawn at a mall...this is a get off the dime moment

[jenni_xx]

Here's a crazy idea... ask her what she means.

So obvious! That's exactly what you should do!

[darla_g]

Pandy you really don't mention, what are you looking for in a relationship? Are you just looking for someone to dress around -or- are you looking for a meaningful relationship?

[jenni_xx]

Interesting, so many here WANT a GG who will go with the dressing and when one finds one they ask "should I?" Really? I read the email as she wants to go shopping WITH Dawn. Your ad says you are a CD, you told her you CD, she is willing to be with Dawn at a mall...this is a get off the dime moment

Just a thought, but half of me is wondering whether she is thinking to herself - with her comment "I think Dawn needs to look pretty" - that she can be a guide for Dawn - and so she doesn't want the OP to turn up, looking great, because that gives her nothing to improve on. Call it a work in process for this particular girl, who may just see herself as someone who can help someone who she may feel is in need of help.

I've just read that back, and not sure if what I actually mean is coming across all that well. Hopefully you get what I mean

[Pandys]

Pandy you really don't mention, what are you looking for in a relationship? Are you just looking for someone to dress around -or- are you looking for a meaningful relationship?

I definitely would like this to be a meaningful relationship, that is why I am looking for the advise, I don't want to mess this up.

[Pandys]

Interesting, so many here WANT a GG who will go with the dressing and when one finds one they ask "should I?" Really? I read the email as she wants to go shopping WITH Dawn. Your ad says you are a CD, you told her you CD, she is willing to be with Dawn at a mall...this is a get off the dime moment

I am not asking "should I" but more how should I. Until being on this site I never thought there was a possibility of a SO that would be accepting let alone supportive of my dressing. I will admit it is weird at my age to be so concerned about how a potential GF perceives me, but then again so is dating.

[Pandys]

My radar would be going off a little that you might just be playing to her curiosity. I'd be very keen to ulterior motives this early on in the relationship.

I would too but in the many conversations, ( and a couple 3 hour phone calls) dressing was a almost never mentioned.

[Madeline80]

Show up in guy mode or androgynous. Bring your wig and some girl stuff in a bag. While you are at the mall, get a makeover and change clothes. You might be surprised at how good you look, and with a female friend along for support it can be a big confidence booster. Probably be fun for both of you.

It's too early in this " relationship" to say I want x, y, or z. Just have fun and let it go whichever way the universe intends.

[sarah378619]

Be happy you have a girl that is accepting. Most good relationships starts as friends. Have fun with her, and show her who you are. You are very lucky to find an accepting girl. Even if she ends up as only your best girlfriend, it will help you develop as a girl in leaps and bounds.Good luck.
Sarah

[Beverley Sims]

Before going out, has she seen you dressed?
If so go for it as otherwise the vision she has built up about you dressed may be shattered.

[Pandys]

Before going out, has she seen you dressed?
If so go for it as otherwise the vision she has built up about you dressed may be shattered.

No she hasn't, we have only met in person once for coffee and talked for an hour or so. Until she mentioned shopping for Dawn we hadn't really discussed my dressing.