Relationship dilemma/question

[Heather1129]

I started a new job about 6 months ago and one of our office girls seems to be interested in me, she is always chatting me up and being very friendly. She asked if I could fix her vacuum cleaner for her among other things. She is the kind of girl I think I would like to pursue, but I am not out and I would like to be upfront with her and tell her about my dressing and see where it goes from there. I don't think I want to give up dressing, even for a short period, its just too much a part of me. I am just afraid that if I tell her its going to get around the office and I don't want that. Its been 20 years since I have been in a relationship of any kind and its kinda like new territory all over again. Comments? Advise? Suggestions? Thanks for any input.

Heather

[ReineD]

Don't tell her straight off the bat. The wise thing to do, is to see if things progress with the two of you romantically first. Fix her vacuum cleaner. Ask her out on a date, if she accepts and it goes well, ask her out on another.

If after at least 6 dates it looks as if the two of you are an item, then tell her.

[MelanieAnne]

Good advice. Wait a while. If you do tell her, do not make like it the biggest thing in your life. You might mention that have explored crossdressing a few times, and get her reaction. If you come across like it is your whole life and you cannot live without it, she will quickly begin wondering what she is getting into, and where she is going to fit in.

[Mink]

[do things] romantically first. Fix her vacuum cleaner.

ok this cracked me up!

how 'bout I fix yr vacuum cleaner, baby...

[Tracii G]

Fix my vacuum has to be the oldest line in the books LOLOLOL.
Be sure your soldier wears an overcoat

[Paula_Femme]

Hello Heather

I don't want to be a Debbie Downer here, but "office romances" are fraught with danger, especially if/when they end. Although I'm a big believer in "full disclosure" from the get-go, in my case I'm talking about internet dating, dating someone in the office adds a whole new level of complexity to the situation.

In this instance I would definitely go with Reine's suggestion, thoroughly read that vacuum cleaner manual(!), then date first and see if there's a connection, and if there is, well, that will be your moment of truth!

My suggestion would be that while you're "dating" bring up the subject of Caitlyn Jenner et al, and see how she reacts... God knows there would be plenty of opportunity as she's pretty well front and center of the Celebrity Gossip Industrial Complex!

If she reacts favorably, or at least sympathetically, later on you could start a discussion about Eddie Izzard - check him out online, there're plenty of videos - he's brilliantly funny... definitely the kind of cross dresser you could introduce to your Mother!

You might get lucky and she will be into your 'dressing, or at least open to it, and on the other hand she might completely freak-out and run for the hills. If she freaks, you obviously run the risk that she'll blab to her friends, and you know how difficult it is to keep a secret in an office, especially one as juicy as that!!!

Similarly if the relationship ends at a later date, especially if it's not on good terms - when is it ever?! - she could blab that your 'dressing was the reason, you only just told her etc, as she probably wouldn't want it to be known that she'd knowingly dated a cross dresser.

So, sorry to be so negative, but in this situation I'd say you have to be VERY careful indeed!

Good luck!
Paula

[Lisa85]

New job and you want to enter this mindfield? Are you ready for CD to be known to your new company? What is plan B, are other jobs easy to find?

I've only seen it "work" in one situation, same company but totally separate group, and that's without any CD. It lasted 18 months, a long fling.

I don't know about the rest but for one I would find it extremely hard to work well with SO.

Not saying no, but don't get caught up in a pink cloud unless you're ready for the full ride.

[franlee]

A couple of things, there is no reason to tell her until you have found that you will be in an relationship that is more serious than dating, unless you intend to CD on those dates, Next you should be sure she is going to faithful with your secret even if or when you part ways. There is a couple of pieces of advise I will offer from bought experience, never get your money and your honey from the same hole and always remember everybody's business aint nobodies business. You can't pull the smoke back in a bottle after you open it and you have to live with the consequences of not only your decision but those of everyone she may decide to confide in.

[docrobbysherry]

I believe closet dressers should tell people only on a "need to know" basis! That's my code.

And, what Reine said!

[Rachel05]

Speaking from my own personal experience, I never told my partner until we were very close, we were very close and it was still a difficult conversation, it is after all quite a shock

I trusted her totally by the time we had the conversation and after the initial shock, we had several long and detailed conversations based around her asking many questions and me answering them with total honesty

The upshot is that we are now together and she is supportive, which is way different to my wife of many years

I am glad I waited until I was certain that we were close, she was happy to know and I was happy not to have to skulk around when I had time on my own to dress

Based on my experience, i would definitely wait

Or alternatively fix her vacuum and then do your best Freddie Mercury impression from I want to break free

Take care

[s.e.al]

Don't be in any hurry to tell her she may really just want her vac. fixed

[pamela7]

the vacuum is like a test that you can do the man thing, so be sensitive to also doing the femme thing, i'd probably consider doing the vacuum but with nail varnish on!

[Tina_gm]

Wow, if fixing a vacuum cleaner is a test of manhood I still pass. I think it is a somewhat unique invitation to get together outside of work.

Now, while I am in big favor of telling early, no need to tell as soon as one fixes a vacuum cleaner. If it is casual dating, and you don't know this person well, you can hold off. But I would always highly recommend telling if you feel it is becoming more serious.

I would also recommend never EVER dating co workers. Been there, done that. It's always great until it sucks, horribly. Multiple problems with the co worker thing. People at work always chat about it. Always rumors swirling about the state of the romance. If you are having some argument people will end up knowing one way or the other. And then there's the break up...

When you break up with someone, the more space between the better. In the case of co workers you get none. It takes forever and ever to get past. And when you date someone else they will have issues that you work with your ex. My advice on co worker dating, run like hell.

[Marcelle]

Hi Heather,

Plenty of sage advice already given with which I agree. I would feel things out in the romance department first to make sure it is the real thing before coming out. This is someone who works in your company and if things go bad on the relationship front, the most you will have to deal with is some bad PR. However if you out yourself and it goes bad . . . you may have a whole lot more to deal with IMHO. In coming out to people I always caution using the "Am I comfortable with everyone potentially knowing rule of thumb". Once your release that information, you loose positive control on it and anyone irrespective of how well you know them, can let that information slip to others . . . just saying.

Cheers

Isha

[UNDERDRESSER]

I also don't like the idea of dating co-workers, but then I found she liked one thing, then another, then another, then what books she reads, finally we both sniggerd at the same weird joke somebody made. Oh crap, '"Hey, do you like Indian food"

To tell her or not. What's the worst that can happen? How likely is it? What do you know of her personality, ethics, attitudes? You know her, at least better than we do. I was certain when I told my GF that I was safe from the "worst possibility" Thing is, at my age and this point, I really wouldn't have been terribly interested in someone who would not have been the type that I though I could tell anyway.

[Krisi]

Paula has it right. Even without the crossdressing thing, office romances can be big trouble when they are going well and when they end. Some employers even have a "no dating" policy although I'm not sure how it could be enforced.

There are plenty of available women out there, leave this one alone as far as romance.

[Samantha_Smile]

There's an old saying (well, might not be that old), and it goes something like,
"Don't poo where you eat"

You work with this girl? Where you're contractually obliged to keep showing your face around her, even if this goes south?
I assume you CD and are not out at work?
All I'm saying it that putting food on your plate will get a whole lot harder if you either
a) Break up
b) Break up after you tell her you CD
c) Break up after you tell her you CD, and then she lets word out and everyone finds out
d) Break up after you tell her you CD, and then she lets word out and everyone finds out and then people treat you differently, maybe even discriminate against you.

Seriously, if you're single, try dating sites.
I know it's weird and still seen as 'nerdy' but that's how a LOT of people are meeting now.
You can pick and choose who you meet without worrying about people talking.

Don't want to put a downer on it if you like her, I'm just saying take care
xx