Surprise getaway, time to tell wife?

[Candace Baci]

Hey Girlies,

Sorry I haven’t been on a few days , not much alone time but I wanted to first thank everyone for your suggestions( please keep them coming, cause I may need them). Wife surprise me on Sunday with a long Halloween weekend getaway, 5 days house rental on the shore.

I was thinking this would be my chance to tell her my secret? My thoughts were to try to convince her that her and I should have our own private Halloween costume party,If she agrees I would pack my things. My thoughts would be to “become” Candy, have several and I mean several glasses of wine and open up and tell my story.

I wish I had the courage as the rest of you, but I think the wine and costume party suggestion might work? Thoughts? I would love to empty my bucket and get this secret out?

[Cath N.]

Let me get the first answer in before you get drowned with a hundred “that would be dreamy!” answers. If you have not told your wife, suggesting you get dressed as a woman while you tell her you are a crossdresser is a big no-no. Halloween playing dress up for a laugh (haha,look at how ridiculous I look!) is not the way to tell your wife something like this. And drunk to boot as well. Seriously, no.

If she booked a surprise getaway, I can promise you you will ruin it. You cannot convince anyone anything. Jesus, whatever you do, do not show up dressed up and proclaim you have been hiding this from her all this time.
Your life, your decision. But this has a 90% failure chance in my book. If you are serious about doing this, I suggest you look at only GG suggestions at how they managed to deal with this successfully, how their SOs sensitively approached the whole thing and,more importantly, what would have made the process easier for them. And leave all the fantasies of your wife being ecstatic at the revelation and throwing herself in your arms outside the door because you have less than a 0,0001% of that happening. Do not make her regret trying to do a nice thing for both of you. As I have left my diplomacy hat outside of this reply.

[Robyn DeVyne]

Thats definitely one way to do it.  And I do understand the stress and fear…and the alcohol! 😀

Not to be a downer or ultra serious, but where is there a “right” time?  Just a question.

My other piece of advice is that you have to make “YOU” a top priority.  So many of us have lived or are living for decades in the closet.  Sooner or later you have to treat yourself as number 1 priority.

Nobody else will.

[melissa la quinta]

Great advice, Donna! You nailed it.

[Mandy Wife]

From the wife side of the fence, I can honestly say I really don’t think this is a good idea at all.

If your wife is surprising you with some time away so you can be together then and just chill then that’s what she is needing just now and it will do you both good to relax I’m sure.

I really don’t think getting dressed en femme and breaking your news is a good idea – I can hear her reaction of “are you being serious” already and, to me, dressing up for Halloween is a bit of fun and diluted your message as frivolous fun rather than something serious.

Have your week away, spend some quality time together and enjoy yourselves, then I’d you feel it’s right to tell her, sit down when you get home and TALK rather than show and be lead by her pace rather than going for the steam-roller effect.

[Robyn DeVyne]

Just want to add that my comments weren’t to pressure you or be critical.  I’ve done it too and its very tough and scary.

Robyn

[Stephanie]

Wife here. Please do not do it this way. If she has booked and planned this then she has an expectation of how your weekend will play out, let her have that. Nothing will be the same after you drop your bomb so let her have one last lovely weekend where it’s just her and her husband. If you absolutely must tell her try to do it on a totally average day and be gentle do not introduce her to “Candace” unless she’s asks.

[Danny Amone]

I have to agree with Stephanie, this is you and your wife’s weekend. Have fun, party. There will be other opportunities.

[Jamie Taal]

I generally agree with everything most others have already stated. To add to it, I intentionally  told my wife on a non-descript weekday that had no of significance event/significance or something the next day (a big work presentation) that might be affected where she can’t get it out of her head. I did this so regardless of the outcome of telling her there was no baggage of a holiday, vacation, anniversary etc forever being tainted and always overshadowed as “that day”.  When I talk to my wife now she hardly remembers the year, month or day when I told her. We still have other special days to celebrate without the cloud of what was discussed. Remember, as much as this is about you, it is truly about her.

Good luck.

[Abbey]

I would agree with most others that telling your wife while drunk and dressed as Candace is not a good idea. I really don’t see that working out well. Because you know the next morning your little confession will be the first thing you will be talking about with her, while you’re hungover.

[Anonymous]

Well I did a similar this this Halloween. My first time fully dressed. Her girlfriend came and did my make up. It was the thrilling, frightening experience of my life.  Now I want to it again without so much alcohol. My wife thought since I did it once it’d be over. Well I guess it’s not because I wanna do it again soon. Best of luck.

[Anonymous]

my thought is dont do anything you might regret while drunk. it might seam like a good idea, but when you sober up and find out you said some things you shouldnt have. its to late.

[Author]

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