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Time To Date Again?


If you’re recently divorced or widowed, look for these clues that you’re ready to step out into the dating world again.

By Carly Milne

ealing with a breakup or the untimely loss of a loved one is certainly tough, but figuring out when it’s time to move on and start dating again can be even tougher. But how do you really know that you’re ready to make that shift from unavailable to available? “I don’t believe you wake up one day and say you’re ready, I think it’s a defining process,” says Carole Brody Fleet, author of Widows Wear Stilettos: A Practical and Emotional Guide for the Young Widow. “And there are different ways to know that you’re ready regardless of what you’re leaving behind.” So what are some of those ways?

When you realize you can be independent
After going through a stint of bad dating
Nights of pining over lost loves definitely have their place.
experiences, Cathy — a 42-year-old divorcee from Hartford, CT — found herself sitting at home one night, where she decided to open a bottle of wine. “I opened it by myself for the first time, and I used a Swiss Army Knife,” she recalls. “And it was easy. I thought, ‘I don’t need my ex, and I’m not the person I thought I was.’” Cathy could do more on her own than she thought she could. It was a small victory, but that moment also gave Cathy the courage to move on to another new-to-her task: killing bugs. Eventually, she waded back into the dating pool and met the man who would later become her husband.

When you can spend a night alone
Nights of pining over lost loves definitely have their place, but knowing when to let that go can be an incredible part of the battle to move forward. “Whether you’re widowed or divorced, you need to go through the grieving process,” advises Kathy Stafford, author of Relationship Remorse. “Until you’re comfortable with being single again, and you’re confident that you can be on your own, you’re not ready to date.”

When you meet someone you’re actually interested in dating
Sometimes, all it takes is meeting the right person — that’s how it happened for Paige, a 41-year-old divorcee from Washington, DC. “I was married for 11 years, and our split was painful but amicable,” Paige
It’s easy to get comfortable and stuck in a routine.
says. “We split in October, and then the following January I met a man at Starbucks who interested me. It wasn’t a conscious effort. I never thought about the consequences, or if I should be waiting — I just went for it.” (Starting a conversation with a stranger is another milestone in the dating-again annals, too — and a very worthy one.)

When your friends know it’s time
It’s easy to get comfortable and stuck in a routine — sometimes so much so that you forget how to live! It’s not always the easiest critique to hear, but when you start hearing from your friends that it’s time to get out there, you might want to heed that call. “I was heavily influenced by my friends to get out, and they were right,” says Richard, 55, a Pittsburgh native who found himself splitting with his wife of 20 years. “I was staying at home too much, and they kept encouraging me to get out and meet people, started setting me up… and it’s through that I developed greater confidence and an interest in finding someone new. And I did!”

When you just do it
Signs and stages? If you’re missing them all, maybe it’s just time to get out there! “I don’t think you’re ever ready until you do it,” advises Jula Jane, author of Secrets to Date By. “I don’t think you should wait for a defining moment, I think you should just go. You can wait forever and not see that moment!” Remember: You can’t play to win if you don’t get into the game.


Carly Milne has written for Whole Life Times, Yoga Journal and Glamour, among other publications. She lives in Los Angeles.
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