Looking for feedback on going out for the first time.

[AllisonCS1]

So, I'm not a perfectionist(especially with spelling... lol... )... I can be somewhat lazy... and have a tendency to wing things...

That said, I do realize that there are things that one should not wing... Going out for the first time probably isn't one of them. I started dressing, or putting more effort into figuring myself out last august. Unfortunately I don't think i'm any closer to that as each step along the way tends to bring more questions forward from my skulking self conscious.

So I've been planning on going out for several months, actually I really think that was a goal that I've always had, but I hadn't set a time for it... too many doubts and uncertainties, but with the exception of little things like indecisiveness over the right dress with what accessories I find myself in a conundrum as to where to go.

thankfully I have a friend who has a gay friend that mentioned four different places in Chicago to go but due to work I'm unable to scope them out incognito as was my initial intent beforehand.

I only get a block of five days off a month with work... It could be split up but in the summer I have other hobbies too and enjoy doing them as well. Just thought I would explain it.


the thing is I'm not really a bar or club person, sure years ago I used to go clubbing and if drunk enough I could dance but that was 20 years and a different knee. well a younger knee.

SO my choices apparently are; a average looking gay bar... a dance club... a bar and grill... or another bar that does drag shows... the first bar might also have drag shows too.

A large part of me would much rather just go shopping... however I don't really feel like I have the confidence to do that. I constantly worry about what to wear... which accessories to choose from... boots or wedges...

So I'm hoping that by choosing one of the four places and going to it, I'll be more confident to do later excursions to things that I actively enjoy.

I just can't seem to make up my mind though. While I've never been to a drag show my sister enjoys them... But I am unsure if I'd actually enjoy that. Plus while I stated that I am not a perfectionist I worry about being seen as a drag queen because to me that is not my intent and a large part of me just wants to go out and be normal(what ever that is)

While I do drink occasionally the night in question I will be driving so that means no booze unless I'm staying for several hours and then it's just one drink. (I'm one of those people whose legal limit is half that of the other masses due to my job and since I love my job I'd rather not chance anything.) But I say that because I'm not sure if I can go to a bar and not drink especially with it being my first time out. jitters and all that.

I supposed that the bar and grill might be decent, I do enjoy eating... but the problem with that is my schedule for the day, it's a 300 mile drive to Chicago and I have a bday party to attend and leave early... My sister in law is putting in extensions and styling my hair since I can't seem to stand wearing a wig. But by the time I'm done with everything that I need to do that day dinner well I don't like to eat late at night unless I have to. (diet conscious) I suppose I could go and not eat but since I'll be with well family it'll feel weird,

So anyway, I just can't seem to narrow the where down... And am completely unsure as to what expectations to have... and more than a bit paranoid about something going horribly wrong escpecailly because I've had some weird and not exactly friendly happening occur in Chicago... like getting lost leaving Chinatown at night on foot and winding up in a not nice area... or being attacked by a show dog at a hyatt... or being extorted by a homeless guy for 60 dollars to get directions out of the ghetto to get to the hyatt.(pre gps)

[Rachelakld]

First - try an early morning coffee shop, have a coffee. Week or so later have coffee & food, within a couple of months you will be shopping
See my blog on how NOT to do it (I was in a s***ty mood when I went out today)

Have fun

[Pat]

It sounds like you're going to be out alone, so I'd start with something relatively low impact -- go to a movie or go walk around a pedestrian mall or museum. See how you do. If you're feeling good, stop someplace for coffee or food. If you're feeling shaky, just bail and go someplace safe to enjoy the first-time-out rush. If you're going to wear heels, put some flats in your bag just in case that doesn't work out for you -- heels in the open streets act a lot differently than heels around the house. The key is to enjoy yourself.

[Launa]

Sorry I can't help you too much in person as we live too far away from each other. All I can say is go out and give it a try. Once you do it you'll see just how easy it is and you'll say I wished I did it sooner!

[Jenniferathome]

I think going to mainstream places is far more comfortable and fun. Think abut where women might go alone: at night to a bar is not the norm.

[Tracii G]

If you have a nice city park close by go in the daytime.Grab a bench and read a book,get some sun,feed the ducks whatever.
Go to a mall maybe and window shop.
I'm guessing you are a truck driver?LOL
Make your first trip out casual like jeans and a top not evening wear or anything fancy just blend in.

[Alice_2014_B]

My first time out was to the post office at night to check my P.O. box; it was a great start before going to a department store.
Aside from the post office at night I've been to department stores to try on heels at night.
I once went dressed up during the day to fill up my truck at the pumps.
Just pick out your outfit and decide on a time and simple place to go.
You can do it!

[Bridget Ann Gilbert]

It seems to me that the better question to ask is not where to go but who to go with. Going out en femme for your first time is certainly nerve wracking. That's where having a supportive friend can really help. My first night out was with a friend who recently came out to me as a lesbian. We went to a gay night club, and although we split up while we were inside, we knew we could always find each other if the need arose. The important thing is you want the night to be a positive experience and to make a good memory. So if you don't have someone to be your wingman or wing-gal, choose the option where you think you'll have the most fun. Good luck and let us know how it goes.

Bridget

[Michelle55]

Wherever you go, be familiar with those surroundings. You will be more at ease and comfortable. Being nervous will draw attention and make those around you look to see what is wrong with the situation and that increases the chances you are read.

I agree with Bridget that having someone with you will help. Without that try to blend in. Choose your outfit and makeup to match those around you.

BTW, practice a lot on your makeup. Many years ago before I went out the first time I took pictures of my makeup and then reviewed them later when I could give myself a more honest opinion.

[Danitgirl1]

Fwiw, I agree that 9 times out of10 where you go is no big deal (assuming you live in a metropolitan area) and that going WITH someone is more important.
I was lucky my first time, I had my wife with me and we met a bunch of tgirls, drag queens etc that I had made contact with on Facebook. A very safe and positive experience that has set me up for a whole range of subsequent outings.
Try and find someone to go out with and then go have fun with them. Wherever you choose to go, it will be fun.
Oh and dont be surprised if you can dance without the liquor...
:-)

[AllisonCS1]

Actually I will be going with my niece, a younger sister and my sister in law, there's a bit of a age gap between us but my niece has a tendency to forget how old I actually am. I really don't have much in the way of friends, I'm a bit too much of a loner. That actually surprised my therapist as she was under the impression that I was outgoing but I'm only outgoing in controlled environments. When I go to a bar I usually just sit there and stare at whatever is on tv even though I don't really watch tv and pretty much ignore all sports unless i'm in a mood for a cubs game..

My sister in law is going to be assisting me with my make up for that night, as I am a truck driver my time practicing make up application is limited and my technique is in need of a bit of fine tuning.

And technically I've been outside before, from my place to my nieces... walked around a hotel parking lot in the middle of night while on a mini vacation and even went through a drive through. but I didn't interact with the world around myself so I don't think that it really counts as going out. I even in the past had hosted a couple dinners with now ex girlfriends and while those were fun it was still sitting at home and that seems to not be fulfilling to me. my point is though is that I have been trying to take small steps to prepare myself but its been one thing a month at a time, which often is frustrating as I know that I need more but don't have the personal time for more.

That said, the lack of personal time is also part of being a adult so I know I have to make do with what I have.

I don't want to give the impression that I don't have friends, I do have a few but only one knows about the dressing and initially she was going to go with but she can't get off from work.

Thanks for the advice though and there are several things i'll be looking into later on when I get a chance but it's time for me to start rolling now.

[Pat]

And technically I've been outside before, from my place to my nieces... walked around a hotel parking lot in the middle of night while on a mini vacation and even went through a drive through. but I didn't interact with the world around myself so I don't think that it really counts as going out.

Were you feeling excited/uplifted by the experience? Does the memory make you happy? Then it really counts. Stepping out on your balcony counts if that's pushing your personal envelope. We're all individuals -- for some walking past a window in their home is daring, others need to skydive into a crowded parking lot while wearing a sequined bikini. It's not the external accomplishment that counts, it's the internal one.

[AllisonCS1]

I'm not really sure how to describe how I felt. I was paranoid. .. A bit scared... those two mostly because I don't think I pass... frustrated... but in general I think that I felt normal, like I was me.

[Dena]

You should have it made with three women. You'll be able to chose how much much you interact with the general public.
If you go to mall, I'd go when they first open up in the morning.

[Jean 103]

Sounds like you will be with friends. I would pick an adult tourist spot. Shops, coffee houses , cafe's and the such. Make a day or just an afternoon of it . I do it all the time. You can window shop stop for coffee or start with desert .

[cheryl reeves]

we went to the city park and walked around a bit,then my wife had the bright idea of driving 20 miles to the next town and go window shopping in wal mart..allison you ever thought to drive dressed..my wife had the idea when i was a trucker,it was a fun filled day,first me driving then her driving and then me changing and finished the day out..it was a blast...

[AllisonCS1]

Well, I'm not sure what touristy spots would be open on a Saterday evening in Chicago, maybe the 50's McDonalds but most of the fun stuff like the musceums and zoos will be closed. I'm not sure when Navy pier closes down.

I've driven underdressed a few times. and wearing yoga pants before but never full out dressed, and provided its not boiling hot Ill sleep in cute night clothes and a corset, and actually the corset helps me not roll around at night thus insuring my cpap mask stays on...

[Helen_Highwater]

As someone who's been going out in public for some time now but only recently actually been into a shop for the first time (always alone) I would say that given you're not a club person avoid those venues for a first time. You'll be adding to the stress.

I recently went to the cinema for the first time dressed. OK you interact with the sales assistant but once inside you're in the dark and can sit and relax. Having family around you will make it much more relaxing. If you go to an early showing you'll have time afterwards to find an eatery and socialize with you kin, interact with the waiting staff and gauge the reaction of the other diners. Having been to a quiet restaurant on my own I can say it turned out not to be that big a deal. Was I read? Yes. Walking alone through a restaurant you will attract gazes. If I'd had family or friends around me it would have been a "normal" group dining out and I'd probably drawn far less attention.

Follow the golden rules; Dress to blend, be confident, smile and don't be afraid to make eye contact with SA's/waiters.

[Chrissi]

Hi Allison...wow you are lucky to have a group to go out with. I was solo, as I guess so many of us girls here are too on their first venture out into the world.

I originally was going to say stay away from the gay bar or drag show (no matter how fun the latter is) and it is more important to go with someone to somewhere simple. But you are doing just that, yay!

My suggestion: As 4 gals; go to a restaurant! Book a reservation and ask for a semi private table...and go have a girl's night out. You'll be in your own little world at the table anyway, and no one, but your server will have any interaction with you.
Now with your girl friends, go to the drag show...again all of the same above, plus they are super fun, and don't worry...you won't be confused for a queen, indeed, you will appear ever more feminine.

I'd still stay away from the gay bar though, for a couple of reasons. They can be cruisey, not always, but it can test your social abilities to deflect some rather strong come-ons. This, by the way is true of all bars, not just gay bars, where people go to meet new people and sometimes hookup. Now by gay bar, I am assuming you mean men and not lesbians, if so, some gay bar patrons get rather testy about being the "show" for groups of girls coming in for drinks and observation. Their attitude is like: "...there are a thousand bars in the city for straight people and 5 for us...really, you have to choose this one...just let us have our own space?" So just be aware of that. (Personally for me, I don't really care, I not much of a bar/club person anyway, but some of my friends and acquaintences are like that.)

Hope you have a safe, fun and totally enjoyable first time out! hugs
Chrissy

[AllisonCS1]

I suppose that I am pretty lucky.. I had a mini break down last August, and I was really surprised on how many family members rallied to be supportive. Long story short mother overheard part of my break down to my sister and outed me to almost all my siblings (6)

I'm not sure about the movies, I'll have to look into what's playing and trying to gget kin to agree on a movie is a challenge in itself. But it is a good idea, and the theaters in that area are a lot nicer than anything I usually have access to at home.

I'm not sure if I would be able to eat though. Then again if it's a pricey place the smaller the order the less damage to my pocket. .. lol.

Though there is a really nice place across the street from where one of the places that have drag shows.

.As far as dressing for the occasion, i'm having my doubts. As not really having gone out before and not really a night owl anymore I had picked several options out, accesoriezed them and then let my sister and niece give me feedback on which one is the best outfit. I had several to choose from as I believe that I might have Wilma-itus(I tend to charge it) and attached is the one that was voted as the one I rock the most... but while in my mind eye I think it's okay my outer eye makes me think that it's too over the top. plus in the pic my make up was horrible(due to getting eyeliner on my contact and not having more solution to clean it off) . and while I love the boots, I don't know... I think I look too... not really sure about the right word

[kimdl93]

I like the coffee shop suggestion, followed by some shopping or even a stroll through a park. Daylight is safer and, for me, feels more like a normal life. And don't fret about being anywhere near perfect. No one will notice the imperfections.

[AllisonCS1]

Well I do like the coffee suggestion and in a perfect world where I had self confidence I would love to be out in the daylight. But every day normal life is a constant enough struggle with self confidence and I have a tendency to skulk about and shy away from drawing attention. I go days with out talking to people to the point of sometimes I think I forgot how to speak. Some days are better than others and sometimes I do feel confident but those days are usually after long relaxing bike rides.

for the day in question, I just have too many time constraints already, a 240 ish mile drive, my nephews b-day party, another hr to hr and a half drive to my hotel, hair cut and extensions with a make up lesson mixed in for good measure. I do study and research techniques on youtube but other than getting a basic idea I feel an actual lesson in person lesson is more beneficial and will help reinforce what I have already been learning.

And while she doesn't have any first hand experaince with make up techniques for cd's I have shared with her numerous tutorials and sites that cover the differences and show what i'm trying to learn. though to be honest I feel kind of weird talking about it with her because she's my youngest brothers wife and there is a 14 yr age gap.

And while a large part of me is worried about imperfections, If I'm going to do this I need to try to minimalize them. I've already put going out off a few times due to scheduling mishaps and I really truly believe that I shouldn't wait anymore. I'm getting really weary of regrets and the sooner I can do this the better... But if I am going to do this then I need to ensure that I do have the time to not take half measures. All in best foot forward, which is why i'm getting the lesson and extensions put in.

I'd do it Sunday during the day as most people aren't really out and about at parks or even coffee shops(at least where I will be as I have a barista friend whom complains about Sundays being dead)but I will have to drive back home, which if all goes well i'll just stay dressed for the trip back home... food shopping... then I have 1.5 days to power cook healthy meals for the road, vac pac them and then freeze them, plus I have 2 dr appointments on that Monday which due to distance will take up four hours of my Monday...

[Helen_Highwater]

Well what your wearing in your pic won't look out of place on a girls night out and you carry it very well.

I think you have way more positives than negatives when considering should I, shouldn't I. One or two negatives mustn't stop you from doing something that you know you really want to do. Having the support of your family is something so many here dream of so don't waste the opportunity. It will eat at you if you do.

[AllisonCS1]

Thanks, I guess that I'm just nervous about what I should be expecting and more than a bit nervous that the outfit will make me look like drag queen or isn't age appropriate for someone nearly 40. Plus I'm not really sure if I want anyone paying me extra attention and thus keep considering going with something a bit more drab and plain. or at least something without the hooker boots.

But going out is something I want to do and a lot of people are right that I should just do it... get it over with and then come Monday talk to my therapist about it.


And once again I will admit that I am extremely lucky for my family... Well siblings anyway...


But I do have another question... A friend and I were just talking and she asked me what would I do when I needed to goto the bathroom?

I told her that I'm not really sure. I would assume that If I was presenting as a woman then i'd use that restroom. But then she mentioned that she was just reading a fb post about how old is too old to bring your son into the ladies room and she said i'm pretty old to be going into the ladies room...

But in turn, how much does it really matter, on occasion I have accidently gone into the wrong bathroom and was unable to leave right away after the realization. I Janitored for a while at a few different places and sometimes the only difference is the little trash can on the wall.

And some places I've been to only had a bucket mounted over a drain for a restroom and it was unisex... pretty sure it was some type of violation but they remained open.

Of course I could always just make trucker bombs, that way if things went south i'd have ammo... (joking...)

[Lexi_83]

Any support groups you can connect with?