Real women give tips on the right time to share your weight loss past without affecting your potential relationship

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Theodora Blanchfield, 31, a social media manager from Manhattan is proud of the fact that five years ago, she lost 50 pounds. In fact, it's a journey she's publically shared in her blog Losing Weight in the City. Yet there are certain people she refuses to spill to: her romantic dates.

"It goes against everything I believe in, but the fact that I used to be heavy makes me feel vulnerable and even embarrassed," says Blanchfield. "I worry they'll think I'm going to gain it back. Or that I'm always dieting and won't be any fun-as if all I do is eat salads and work out." (Enjoy dates, happy hours, and more with these Weight Loss Tips for Every Weekend Activity.) Unfortunately, that fear was confirmed for Blanchfield on a recent first date. A female acquaintance shouted across the bar, "I love your blog!" prompting her date to ask Blanchfield what the blog was about. She told him-and never heard from him again.

Blanchfield will never know why her date disappeared, but experts agree that it's wise to wait until you're several dates in before sharing personal information like weight loss. "If one of your date's first impressions is the knowledge that you've just shed a substantial amount of weight, he or she will see this as one of your main defining features," explains Mimi Tanner, author of The Reverse Ultimatum: Get A Commitment Without Conflict. So how exactly do you tell about your past?

Frame It in a Message of Empowerment-Not Shame

"Instead of saying ‘I used to be fat,' try saying, ‘I started training for a marathon a year ago, and I lost a lot of weight. It was great,'" adds Sara Eckel, author of It's Not You: 27 (Wrong) Reasons You're Single. "Most people want to learn how you did it. You took control over something in your life." Work the topic into conversation nonchalantly rather than dropping a bombshell. (After all, you're just sharing that you used to be a different size-not that you robbed your neighbor's house.) Blanchfield-who recently changed the name of her blog to The Preppy Runner-has adopted this new approach. "I purposefully minimize the weight loss and emphasize the fitness," she says.

Timing Is Important

It's tempting to want to show off the qualities that helped you accomplish such an impressive goal. Who wouldn't want to date someone who has a demonstrated track record of courage, commitment, and self-discipline? If you have to come up with a number, the fifth date is the best time for the big reveal, says Tanner. "They will already know you by then and will be able to incorporate this new information without it damaging their tender first impressions," she says. (For more timing advice, read The Right Time to Talk About Everything in a Relationship.)

Perhaps a better indication of the right time to tell, though, is when you feel ready. "You're not obligated to tell everyone your whole life story off the bat," stresses Eckel. "It's better to come from a place of self-respect. Instead of thinking, ‘Will he judge me?' think, ‘Do I feel comfortable giving this person this information?' You're giving yourself the power."

Ilyssa Israel, 39, an executive assistant from Springfield, NJ, felt so comfortable with one man that she told him on the second date that she had lost nearly 100 pounds after undergoing gastric bypass surgery-and had gotten additional surgery to remove the excess skin. His response: "Great! Good for you!" Then he confessed his own struggles with weight and body image. "I think telling him early on brought us closer," says Israel. "We could tell each other our deepest darkest secrets and be completely accepting." They married two years later.

Control the Controllables

No matter how craftily you communicate your past, you can't control how others hear it. Be prepared for some to be shallow or superficial, adds Eckel. But know that sometimes, people surprise you. Blanchfield was touched when one guy she dated told her she had inspired him and later, he lost a substantial amount of weight. "It felt nice knowing that changing my life and putting it out there had a positive effect on someone else," she says. (Add that to the 6 Not-So-Obvious Signs He's a Keeper.)