SO 'date night'

[Fi Evo]

We're going on holiday in a few days time and my SO and I have planned a 'date night' it being a completely different part of the country for both of us.

Where we'll be staying has a couple of bedrooms so we can both get dressed seperately for our night out (as I know I'll take the longest).

I've bought a new outfit, including the cutest handbag, and have been practising my hair and make-up for weeks.

Whilst my SO knows and enjoys the fact I dress it'll be the first time that she's met Fiona and the first time I've been out in any meaningful way.

Any tips? :)

Fiona

[Linda E. Woodworth]

WOW!

I am so envious of you.

The only tip I can think of is take things slow and enjoy the evening!

Good Luck and let us know how it turns out.

[hope springs]

Worst case scenario she screams in horror upon seeing you and as you make a mad dash for cover run into a biker gang of bigots.
But i doubt the above, so ill say not everyone looking at you is guessing your gender, smile and move on. Focus on having a pleasant evening with the wife. All else will fall into place. Please update us when the big event happens

[Jaylyn]

It is fun when they meet their SO or wife and your dressed for the first time. My wife told me that she needed to meet Jaylyn and told me to be dressed one day when she came home from work and that she felt she wanted to meet Jaylyn. I remember being so nervous that it took forever getting my makeup on right. I wanted every thing to be perfect. I met her at the door and introduced her to Jaylyn. I thought it was going to be awkward but we sat and visited like two girls chatting the first time and she now thinks of Jaylyn as a separate person. She even buys Christmas presents for her. I also try and not do too much dressing around her except for small things like maybe painting our toes and such. I love my wife and she married a man so I present that way to her most of the time. I know you two will have fun on your night she meets Fiona.

[Kris Avery]

Jaylyn,
That is so sweet. You have a wonderful SO and I loved the part about Christmas presents for Jaylyn too. awe

[bridget thronton]

Sounds like a great trip

[Ashley Lyn]

SO and I sorta' planned one of those during a trip we had to make with an overnite stay..
Ended up at a motel where a bunch of construction workers were staying.. :eek:
Needless to say, even tho' I don't look that great dressed, I chickened out for the SO's sake!
I gotta' plan better.. I stayed in the 'closet' that evening..
Have fun!!!:battingeyelashes:

[JayeLefaye]

Awesome!!! As for tips, I have only one, actually, two.

1. If you can walk out of your room fully confident that everything's in order, then strike a pose and go "Tada!"...But if you're having trouble with your make-up, then don't waste 45 minutes trying to get it right. Do everything else, and ask for her help. She's been doing make-up a lot longer than you have:-)

2. Remember and remember and remember, that this "event" is NOT just about you!!! She is going to see her husband in a dress for the first time...And YAY for her being soooo supportive...But it will, nonetheless, be a "system overload" for her...So feel free to compliment HER on how good she looks!!!!

Actually, I have a 3rd...

3: Your "date night" is gonna have a ton & ton of pressure to get it perfect. So many emotions, so little time...

So, my suggestion would be to plan 2 date nights...

One night of introductions...And maybe it all goes smoothly, but golly, there are gonna be emotions involved!!!

So, take the first date night as a test run, and maybe order room service while you both explore feelings.

And then have a 2nd Date Night the next evening to actually go out and enjoy yourselves with your newfound relationship(S)...

Bottom line? If you're only planning one "date night", then you're both putting way too much pressure on yourselves to get it right...

Let the first night develop as it will, with no expectations, and just go with wherever the flow takes you, because you know that you have a...

...A second night to have fun with it!!

Congrats on having an SO who wants you to be happy!!! And so she's giving you this Gift...Give it right back to her, because SHE deserves to be happy too!!!

Jaye

Edited to add:

My SO & I have a local "Date Night" once a month now, and we have a blast every time!!! It took her a while to get to this point, and required patience on my part...But oh so worth it!!!

[Henriette7]

Good luck, all the best and let's know how it's going :-)

Love
Henriette

[Fi Evo]

Jaye,

Thank you for taking the time to 'pen' those words it is genuinely appreciated.

Lots to think about including some insights I've never considered, especially returning my SO's understanding and thoughtfulness.

Thankfully I've got some time to plan :-)

Fiona

[JayeLefaye]

And that was "penned" from my iPhone with my thumb:-) Glad it helped...

This is a Journey...And you have a great First Mate...But you already knew that, didn't you:-)

And full disclosure? A lot of what I wrote was due to my having reading the GG threads on this site, and adjusting my own "perspective" accordingly:-)

Jaye

[charlenesomeone]

Sounds wonderful. Have a great time. So lucky.
XX

[Eryn]

I love going on "date nights" with Mimi! We go out together once or twice per week.

First encounters are always somewhat emotion charged for both of you. We're desperate for acceptance and they're, well, hoping that thing go well for both of us.

Plan to do something that is enjoyable for both of you. Focus on the activity, the fact that you are doing it while presenting as you wish is icing on the cake. Keep it simple and light and don't try to cram too much into the evening. You'll have plenty of opportunities in the future!

Don't expect your SO to be your makeup artist, hairdresser, or fashion consultant unless she would truly enjoy those roles. You're a big girl and should be able to fend for yourself. That doesn't mean that you shouldn't help each other, but remember, she's your friend, not your tour guide to Girl World!

Dress sensibly for the activity. This isn't the time to live an adolescent fantasy unless you happen to be an adolescent. Do coordinate your outfits as any GG would.

Don't sweat the small stuff. It's easy to obsess on the minutiae, but no outing is perfect. If you stop having fun so will she, and neither of you want that.

[kimdl93]

Hope you both have a date night that yields many fond memories!

[Fi Evo]

Thank you all for your help with this, very kind and as a new member here I'm touched at how supportive you all are.

Update: My new handbag arrived yesterday, my SO spied it and she asked to borrow it for a forthcoming wedding we're going to!

[Dorit]

My wife and I go out as sisters a few times a week, but so far never outside the house. We have this game we play together where one of us picks a world capital and an event, and then we dress accordingly. We love it and have a wonderful time together, and besides it is much cheaper and non-threatening to do it all at home! We talk about sometime doing it for real, but as we live in a small town, it would have to be on one of our trips abroad.

[raven_crossdresser]

You are going to probably be nervous so just be yourself and have fun.

[Fi Evo]

My SO asked to see me in my latest wig yesterday to (as she put it) "make it easier to meet Fiona". To say I was nervous was an understatement, but it went really well and thankfully she loved it and said I'd made a good choice.

This little step helped enormously as we had a great discussion about my CDing and the fact that she enjoys it. Later in the day we went clothes shopping together, she bought herself a new dress and she picked out some 'girlie' nightwear for me which she insisted I wear to bed.

We're both now looking forward to date night with much less pressure!

[JayeLefaye]

Oh Fiona, I'm so happy for you!!!

She borrowed your purse and likes your wig. At least you know you have good taste:-)

Now take a deep breath, and don't push it too much as she continues to wrap her mind around this. But WOW!!!

Hope you have an awesome trip!

Jaye

[Marsha My Dear]

We have a long weekend planned. Marsha will be out and about for the first time. My only advice-own the moment. Please pass along how it goes.

[Fi Evo]

An update, i bought a new outfit for date night, very cute but understated pleated wool mini skirt, skinny ribbed jumper, charcoal tights and some suede wedge courts. Rather than hide my purchases as i've done in the past I showed my SO immediately on bringing them home. I also asked if she wanted to see them on which she did.

Some hasty dressing later (forms but no wig or make up) I gave an impromptu catwalk show, to some very positive comments, particularly about my legs! We've now agreed that this will be my outfit for date night and have even talked about which perfume I can borrow to go with.

My darling SO has now seen everything for the big night I just need to put it all together and get my make-up just so!

Wish me luck girls! :)

[justmetoo]

Good luck, Fiona! Sounds like all of your preparations are on track. I hope you can just enjoy the date and not worry overmuch about the details and laugh off any missteps especially things outside your control. Have fun, both you and your wife (she sounds pretty cool)!

[Beverley Sims]

I only think don't try to be too girly.
Look at how more mature women interact, I mean those about thirty.

[Krisi]

Good luck on your date night.

I only wish I could do the same with my wife. Like so many wives, she is a bit up and down with my dressing and right now it's a "down" time. We'll be going out of town for a weekend soon but it's only a couple hours away from home and it's a festival so people we know may show up there as well. That pretty much kills the chance of us going out as sisters or girlfriends even if this was an "up" time. :sad:

[Fi Evo]

Well date night didn't quite work out as planned, but so much the better.

After far too long getting ready my big reveal was met with great enthusiasm and fantastic compliments, but my SO was too nervous to go out. I plucked up all my courage and ventured out alone for a drive and a walk, all fun and no dramas.

My SO is now so encouraging and helpful and it's opened a wonderful and supportive dialogue between us.

We've since been dress shopping (I got a great new frock from a sale rail) and another night later that week Fiona made another showing and ventured out again, different outfit, different make-up - again with much support.

Possibly the best result.

[Krisi]

It's a shame she didn't go out with you, it seems to me that would be the ultimate in crossdressing, going out with your wife as "girlfriends" and doing normal things two female friends would do.

Ask your wife to help you chose clothing and makeup and maybe at some point she will agree to go out with you, especially if you go out of town where people won't recognize her.

edit: Well there's one thing that comes to mind that might top going out with your wife as girlfriends but I'm going to leave that to the imagination.