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Wow what a dilemma.
Tell her beforehand and risk ruining the holiday or wait till after and have you stressing about what could have been.
I don't envy you at all.
However you know your wife best. How about a nice meal out somewhere and sound her out before committing to any drastic action.
Sorry not to be of more help.
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Wow 50 lbs I am jealous so congrats on the weight loss.
I would not ruin the vacation and discuss it after the trip.
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Paula, are the kids with you or are you going just together on this trip ?, that would make a big difference on when to ask
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As an update to my earlier request for help after weight loss and having the final talk with my wife. I greatly appreciated all the advice given on how to approach this and end the end decided to tell her early and rip the band-aid off so to speak. I started off by asking for her help in getting my body toned back up and then I told her about my motivations for the weigh loss. It went well - baby steps as she said - i reminded her i told her about this a long time ago before we had kids and then we paused for kids - I told her about the things I would like to wear - she said so you want to dress like a girl - I said no - just on the inside and never outside the house - - she did admit I have female and male habits - I think she might have guessed my motivation for losing the weight - especially since she saw me and approved of me getting a tan while wearing a speedo or a bikini as she called it - so I will be wearing a nightgown on our vacation on a trial basis - she did say it may not have the desired outcome I am looking for - so we will see - Thank you all!
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The last sentence about the desired outcome what did she mean by that ?
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I originally told her way back when that I wanted to look sexy for her and then later I said I found her lingerie to be beautiful on her and I would like to wear something like that as well - hence you need to lose weight - so that was my motivation - so she was saying she might not see me as sexy in it and find it attractive on me - but she didn't say she won't like it all - so hope springs eternal
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She hasn?t forgotten. Put her first and then she will see that you concern is for her. Otherwise it is likely to be perceived as selfish.