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Honestly, there's such a thing as being too up front about a subject. When they ask about your job, just ask them why that's important to them. It'll make them justify the question and you'll be better able to weed out the gold diggers.
As for dating experience, only way to get experience is to get out there and be proactive talking to real women (see below for more info). Sitting around waiting, hoping, the woman of your dreams falls into your lap is foolish to say the least. If you need a tutor to get better at attracting and dating women, like you'd get a math tutor or go to drivers ed, then look up dating coaches in your area. There are tons of them out there these days. I also suggest joining Toastmasters so you can learn how to present yourself in terms of public speaking: tonality, voice projection, eye contact, and minimizing nervous movements like fidgeting, vocal pauses/filler words, etc.
Don't settle for "being yourself". Instead, be your best self. As for gaining confidence, that comes with experience, and that's where a good dating coach comes into play. They'll give you drills and exorcises to do to get some experience, plus a structured framework to follow so you can slowly improve your skills with actual women.
Honestly though, the crossdressing thing is a huge deal. I'm not going to say you should stop, but I will say you need to accept the reality that it's going to put off a ton of women who might otherwise be interested. You've got to make a decision and figure out what's more important to you.
Some good advice. And Jesse, if you are not working, you have the time to invest in working on these skills. You also have a boatload of stuff you can sell to pay for a dating coach and maybe some therapy to help with the hoarding. I've seen your posts where you catalog all the clothes you own: how many suits, how many skirts, how many swimsuits, what sizes they are. It's obsessive.
If you are looking for a woman who will not be turned off by your cross dressing preferences, I recommend interacting with various fetish communities online and in your local area. There are dating sites for people with alternative lifestyles. I don't see your clothing choice as a big deal (many straight men like to cross dress some of the time). As another poster mentioned, however, if you are unsure about which gender you wish to be, it's best to resolve that before pursuing a romantic relationship. You should also seek counseling for your anxiety and paranoia, as others have mentioned. Self-confidence and self-acceptance are important qualities to develop before you commit to someone else or have children. Don't find a wife and have children out of the fear of loneliness, as that will likely lead to you latching on to someone who is just as desperate. Marry and have kids, or adopt, when you yourself are stable and thinking clearly.
You should also keep up with the job search. You may have to dress in male clothing for work only, or find a work from home/online job to solve that problem. In an ideal world, one's personal style wouldn't matter in the job place (I say this as a goth girl who tones it down for academic conferences), but you may have to compromise for a work situation. It would be a small price to pay for economic stability, which would help you achieve your goals.
Another thing...your subject heading states that you want a woman "pretty enough." Are you overreaching and idealizing here? You should of course be attracted to your prospective girlfriend, but consider dating women closer to your age to increase your chances of success. Women in their mid to late 30s can still bear children....hell, even 40 somethings have kids. Good luck to you.
Dude, seriously, WTF is up with you? Instead of asking god to bless you with a good paying job, you need to ask him to help you with your mental issues so you can get off that medication and ask for help with this whole crossdressing ridiculousness. Seriously. Look at your friggin profile pic, its crazy and it creeps me out. Have a friggin' yard sale to get rid of all those female clothes.
Oh my god, I so agree with Lao for the first time ever.
It isn't just the cross dressing though, it's the whole persona of Jesse69.
Another poster said a gender reassignment is in order and I agree.
Whatever the case this OP has serious issues and will end up a lonely old cross dresser if he doesn't get psychological help soon.
Oh my god, I so agree with Lao for the first time ever.
It isn't just the cross dressing though, it's the whole persona of Jesse69.
Another poster said a gender reassignment is in order and I agree.
Whatever the case this OP has serious issues and will end up a lonely old cross dresser if he doesn't get psychological help soon.
Yeah, the OP needs to figure out how to totally reinvent himself in a positive manner. A life coach and a therapist will help. Make sure you find a GOOD therapist who has many positive references. I had some serious issues years back and went through two bad or mediocre therapists until I found one that correctly diagnosed me with adult ADD which was causing some serious depression. I'm 35 and grew up in the days where ADD/ADHD was relatively unknown, so I've probably had it most of my life. I was placed on Ritalin and everything is all good now.
You have been unemployed for over 2 years
Your mom lives with you
You are 42 but still don't know what is and is not a financial "asset"
You support yourself via government handouts
You are mentally unstable as per your own admission
You are a cross dresser who favors the wardrobe of a 55 year old woman...
And yet you feel you deserve a younger wife who is "pretty enough."
Is that right? Have I assessed the situation properly?
I'm 42 and have been unemployed since Aug 15, 2008. An unemployed man is like dateless material. I had a good conversation in a park with a woman and got her email but later when I emailed her she didn't reply back. The only assets I got are my $34,000 bike collection, $25,000 in size 4 to 8 women's clothes, and a 3 story remodeled house in Wicker Park Chicago. I also collect $1095 monthly SSDI and have full Medicare A & B and Medicaid.
What keeps me from being lonely is that my mom lives at home with me now, but in 6 months she will fly to the Philippines to be with her husband. I will be alone and that is dangerous because sometimes I get paranoid or panic attacks and it's good to have someone nearby to keep you company and stabilize you.
My ultimate dream is to have a wife and two kids; one boy and one girl. But I have often been discriminated in the workplace when they called me gay for being a crossdresser. Yes, there are rare few women that marry crossdressers, - and I have to find one. I look at the women when I go to grocery stores or the shopping malls, but I haven't found one. Tomorrow I will go to a job fair and will look there too.
At 42 I feel too old to date a woman in her 20's. But many times people say I look young like a 28 years old because I'm fit and slim enough.
I have no experience dating a woman. I only kissed a girl in preschool and never since. I never had a girlfriend in elementary, HS, college, and after college. So I have lived a lonely life except for family. When my parents and aunt dies I will be one very lonely man.
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