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Ask E. Jean: How Do I Explain My Extreme Shyness?

Dear E. Jean,

Whenever I meet a girl I don't know, I suffer from truly spectacular social awkwardness. It's difficult for me to function at any level, including breathing. The result: I'm 40, and I've never had a girlfriend. Never even come close. I've gone out on three dates in my life, each one a disaster. It didn't help that I lived at home into my mid-30s — way too long, I now realize. I'm trying to change my life. I've moved out, bought a house, and have been working hard to overcome my shyness. I've begun having conversations with people I don’t know well. To my immense relief, I'm getting better with practice.

So the question is, now that I'm working up the courage to begin dating, how and when do I tell someone about my odd case history without throwing them for a loop or appearing to be way too peculiar and turning them off completely? Yes, I'm also worried that I'll make every other dating faux pas in the book, but one problem at a time. (Please, please, please no 40-year-old virgin jokes.) — Self-Conscious Enough as It Is

To read E. Jean's advice,


Self, My Swordsman,

I beg your pardon. Did you say . . . three? Only three disasters, sir? Hell, there are hundreds of social catastrophes for you to enjoy. Get ready. Here are your five steps to victory:

  1. Lay Plans: Go to your local church and sign an "abstinence pledge." Statistics show you will lose your virginity within seconds after leaving the building.
  2. Know Your Weak Points: Don't date. It will kill your social life.
  3. Vary Your Tactics: Instead, go to It's genius! Scroll through the dozens of inspiring, egg-heady, wild, world-bettering get-togethers in your area and choose a group that you like. (Yes, there are "virgins" meetups, not to mention the "Beltway Atheists." And if you don't join a group that is at least half women, I'm going to come to your town and hold a meetup called "Bang Jim.") Then all you have to do is show up. Shake hands. Share a beer. No pressure. Make friends of all ages and both sexes.
  4. Wage the PR War: Your story: single guy, a bit shy, good job, owns his own home, no baggage.
  5. Allow Yourself to Be Conquered. And when you get effed-up and shaky in the middle of a conversation—excellent! Most young ladies will walk over their own grandmothers to find a man who will listen to them. (Sun Tzu says the warrior who "gathers the highest intelligence" achieves the "greatest results.") So don’t worry. Wear something handsome, look her in the eye, ask a question, listen, throw out a compliment, ask another question, and in a few weeks you’ll be poking like blazes! Good luck!

To see more advice from E. Jean, visit Elle magazine and

Janine22 Janine22 8 years
Hi OP I am a Psychology student about to graduate. The thing that you mentioned about your breathing problems tells me that it is very likely that you are experiencing anxiety attacks, and it is also very possible that you suffer from social anxiety. If you get a racing heart beat and breathing problems this is a classic panic attack. I think you should consider cognitive behavioural therapy. It has been shown to be very effective at helping people to deal with panic attacks/disorders. It will teach you relaxation techniques and thought techniques to help you deal with the anxiety you experience. Please consider this because I really think it could help you. You could talk to your M.D. for a referral. Good for you for trying to conquer your shyness, and I really agree that the more you practice it, the less insecure you will feel. I think there are many women out there that would be pleased that you are disease free and feel like you have been waiting just for her. I am sure you will meet someone great. Also, I would suggest that if it is an anxiety disorder, that you explain this to the woman. Many women suffer from anxiety and depression at some point in their lives and will be able to relate to this feeling. I would just wait a bit, go out on a couple dates before you get into it with them. Good luck to you.
theavalanches theavalanches 8 years
not at all uncommon. i meet a lot of guys that can't get a date because they just generally don't meet a lot of single women and when they do they don't know how to behave around her. they get into the 'good friends'-zone and that's not where you want to be! i say just hone in to the one girl that makes you feel most comfortable with.
snowysakurasky snowysakurasky 8 years
here's a bunch of random advice dont worry so much! in a way u still have the upper hand as many women your age have a biological ticking clock--even gorgeous celebs like drew barrymore~! so many women do really want to have a family with a kind, stable, and clean man (and owning a house is a bonus) i wouldn't act too mysterious or people might be worried that you are hiding something like a criminal record. i would not be totally put off if a guy admitted he took too long moving out, as long as he was working and independent in the present if socializing with new people is that stressful, have you considered hanging out with foreign ladies who have not as good english skills? i was shy about dating when i was young but a lot of foreigners approached me when i lived in paris and it helped me build dont have to be as witty and it can feel less awkward!
acyl acyl 8 years
I wonder what this guy does for work? Maybe he has the option of changing jobs to one that offers more social opportunities. I know you're not "supposed to", but workplaces are some of the best places to meet people; hell, my current boyfriend of 6 years and I met at work! (But I do agree it's best to look outside your immediate department--you don't want to run into them TOO much if it doesn't work out!)
EJean EJean 8 years
P.S. Love some of the advice! Dear Sugar is EXHILARATING!!!!
EJean EJean 8 years
My Dear Sugars, The letter is from a man. I have corresponded with him. Def. Male.Male. Male.
bchicgrl bchicgrl 8 years
Well i think because the first sentence of the letter says "whenever I meet a girl" that being said I'm going to think its a guy writing this. I think E. Jean's advice is great and funny at the same time. He made a good move though, getting out of his parents house. That's a huge killer especially when you are in your 30s.
babysoftpink babysoftpink 8 years
Assuming that the letter is coming from a lady, I think the answer is really simple. I don't the key is worrying about how to explain it but rather what you could accept in a relationship, do you want your partner to also not have any significant relationships before or can you accept a man your age who has a long list of sexual history and has divorced twice. I think those are the things to think about? For me, I won't date a guy if he minds my past so much. If he really loves me then he would also try to accept my past as well, good or bad. Thanks.
babysoftpink babysoftpink 8 years
yes, bellasugar, I wonder the same too. Why would a guy visit an "almost all girl site?" There are other men site out there for relationship issues. (Declaration: I am not trying to promote other site but there are and you can just find them easily by doing a simple "google" search) Thanks.
jessie jessie 8 years
real smooth e jean...make fun of the man first thing......not nice!
Beauty Beauty 8 years
I second Meetup — but I wonder if this letter could be from a lady, too.
hope2be hope2be 8 years
Beside what E. Jean has suggested (I LOVE, in my town, they have wonderful activities and wonderful people and they have mingle nights as well as smaller groups that are suitable to your interest), and Fallen (hiring a stylist sounds great, because after all, presentation of outer appearance may make a great deal of difference when you go out there), I'd probably suggest looking into things like life coaches or something like that, or read self-help books during your free time maybe those will give you ideas how to build up confidence. Don't get discouraged with your lack of experience, many women find this attractive (shy guys are cute as long as they're not obnoxious when you get to know them), you may have less baggage. And do the 'don't ask don't tell' thing, don't volunteer information on how you lived with mom until like 35 or something. Focus on the positives, good job, house, financially secure, etc. Also, find out your interests and focus on them, when you have passions and keen interests on things, it's also very attractive. Do lots of traveling if you can, it gives you lots of new experience. Join cruises or what-have-you, have fun.
MissJules5x MissJules5x 8 years
i dont think that your past with women (or the lack thereof) is a huge problem. i think its only a problem because you think it is. its not necessary to go into detail with someone. if they ask you why you haven't been in a relationship in a long time- offer up other reasons... you have been busy with work, and making sure you were financially secure and emotionally secure before you committed to anyone in particular. you can tell them you knew it was a time in your life where you weren't ready to settle down, so you never pursued anything seriously, and that now you are ready to do that. you don't need to go into the bad details. talk about what you are interested in. find things that you enjoy doing and that will definitely help you with the conversation aspect. women like when you are passionate and interested in things. with time you will gain that confidence and hopefully you will find someone that will be right for you.
pioneers pioneers 8 years
My boyfriend has always been really shy-- a good way to make her feel comfortable is to tell her straight out. "Hey, just so you know, I'm pretty shy. I don't want you to take it personally, it's just how I get sometimes." That seems to work well, because it lets women understand your behaviors. The best way to approach your history from a PR standpoint is to be the, "reformed" type--that is, you used to let your shyness interfere with finding happiness but now you've metaphorically, "seen the light" and have taken control of your destiny. Women love stuff like this--it shows that you're evolving, motivated and self aware.
melizzle melizzle 8 years
:rotfl: at the abstinence pledge.
Fallen85 Fallen85 8 years
Maybe invest in a stylist so they can dress you up. Right now your outfit might be screaming "40yr old virgin who is desperate for love and lived with his mom til he was 35!!" and you want it to be saying "sexy confident bachelor looking for love" Also key... confidence is sexy. If you act confident you will become confident and women are attracted to that. No reason to be ashamed of your past. If you act embarrassed by your past then women will act like you should too! If you act like it's not a big deal then women will act like that too. Good luck
scotlandrulz scotlandrulz 8 years
^ totally agree
skigurl skigurl 8 years
uh, yah, like EJean says - don't tell them stuff they don't need to know don't offer up that you only moved out of your mom's house last year...if she asks, make up a reason why and change the subject to make yourself sound cool there's no reason your past should haunt you
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