Q. I’m 44, an entrepreneur and single mother to two adolescents. I’ve been to hell and back in my life and am more than capable of accomplishing whatever I set my mind to. Except in one area. Why, oh why do I find it so hard to ask a man to a movie or out to dinner? I’ve been burned a lot so it’s hard for me to put myself forward, but I really am tired of not feeling like I’m in the driver’s seat when it comes to dating. — Rachel A. Nice girls don’t ask boys out. Like many now forty-something women, Kathy Stafford received this dating advice from her trying-to-be-helpful mother. While on a rational level you know this bit of wisdom has passed its expiration date, subconsciously it may still be working on you.Stafford, 45 and author of Relationship Remorse, says, "Times have changed and it’s now common for women to make the first move. To ease fear and insecurities I advise women to ask a man out for a cup of coffee or quick drink. It’s more like meeting a friend than a date. It’s not such a big deal if he turns you down."Another mind-mojo trick: Since you’re an entrepreneur, think of asking a man out as akin to selling yourself in a business deal. That’s in your comfort zone. According to Jess McCann, author of You Lost Him at Hello, "It’s about your belief system. You believe you’re a good boss who can take charge with coworkers. You’re also comfortable taking charge with your kids. Where you’ve got to do some work is on your image of yourself as a sexy, deserving woman." Believe in your product and it’ll sell through the roof.It takes many cold calls to make a sale. Success is not about a great win-to-loss ratio. Rather, it entails not giving up. As you’ve amply demonstrated over the last 44 years, Rachel, you’re no quitter. Keep taking a chance. Allow yourself to be vulnerable. Flex those assertive muscles. The more you flex, the easier it will become. Ask Jamie Thompson. A 46-year-old divorced Seattle Web designer, Jamie shares, "I recently did the gutsiest thing of my life. While having dinner with a girlfriend to celebrate our birthdays I spotted a very attractive man about my age, alone and sitting a few tables down." Jamie obsessed throughout the meal about saying hello but kept chickening out. Finally on the way out she gave her e-mail address to the hostess and said to tell the attractive man that if he was available and interested to contact her.Did he? Yes! Was he the love of her life? Alas, a dork. Married to boot. But taking such an adrenaline-inducing risk was exhilarating — and habit-forming. She’s since initiated e-mail exchanges with a man in her dentist’s waiting room and with another in line at Starbucks. One contacted her; the other is cyber-AWOL. No matter. "I’ve learned something new about myself. I’m not fearless, but I don’t let fear paralyze me." She giggles, "In a nonsexual way, having that knowledge about myself is orgasmically empowering."Hmm. I’ll have what she’s having!More information on the experts mentioned in this story:Kathy Stafford, author of Relationship Remorse Jess McCann, author of You Lost Him at Hello Do you have a tough question about dating or relationships?E-mail Sherry at DatingExpert@More.com and your question might be featured in an upcoming column.E-mail Sherry About Sherry AmatensteinSherry Amatenstein, LMSW, is the author of Love Lessons from Bad Breakups and Q&A Dating Book. She runs dating seminars around the country and does private coaching — not to help singles marry in 60 days, but to uncover their blocks. She has given relationship advice on the Early Show, Regis, Inside Edition, CBS News, VH1, BBC, and many other programs. Her philosophy is that the most important relationship you’ll ever have is with yourself.Schedule a one-on-one coaching session with Sherry Buy Love Lessons from Bad Breakups Buy The Q&A Dating Book Originally published on MORE.com, August 2008.