The way you express yourself can take the edge off the situation for both of you, says Mary Rader, coordinator of the Frederick, Md., chapter of Over 30 Singles Social Club.
She says one way to initiate a date is to ask the person if he or she would like to go hiking one Saturday. If the person agrees, say "How about this Saturday?"
"You leave a loophole where you're not putting the other person on the spot," Rader says.
Alan Pedersen, who coordinates Over 30 Singles activities in Montgomery County, Md., says it can be as simple as asking someone to have a cup of coffee. That's a good way to get to know each other, he says.
The word "date" itself can be intimidating.
It doesn't have to be a major social undertaking - a date occurs any time you make plans to do something, Diamond says.
He says scheduling a date for nights other than Friday or Saturday takes the pressure off both people and makes them more comfortable.
Diamond says going to a movie isn't a good choice.
"The whole purpose of a first date is to get to know each other, and it's awkward sitting next to someone you don't know for two hours," Diamond says.
Being in a movie theater is a slightly romantic situation, and you have to worry about things such as whether to hold hands or put your arm around the person, he says.
Dinner in a fancy restaurant also could make you uncomfortable.
"You need somewhere fairly quiet, someplace you can sit and not be bothered constantly by a waiter or waitress," Diamond says.
When you're on a date, your former relationship isn't a good topic of conversation, Rader says. Instead of griping about your ex, she suggests discussing your job, interests, hobbies and children.
A second occupation?
Diamond said today's dating scene is difficult - even when you have found that special person, it often is tough to get a commitment.
The quest can turn into a second occupation.
"You have to consciously figure out how to meet someone, and a lot of times that's more stressful than your primary job," he says.
Rader's advice is to join a social group and begin forming friendships.
Some people make the mistake of looking for one special person, and if they don't meet him or her, they are depressed, she says.
"When you least expect it, that's when you meet someone," says Rader, 50, of Frederick.
Rader was married 24 years, until her husband left about four years ago. The breakup occurred as her two children were leaving for college.
"I stayed in for about a year. Then I decided it was time to go out," she says.
Returning to the dating scene after many years of marriage is a scary proposition for many, she says.
Pedersen, 49, a Frederick resident who was married for 22 years and has been single for eight years, says it doesn't matter who does the asking.
"It always is a two-way street," he says.
He says the process takes courage.
"Don't worry about rejection; just go ahead and ask," he says.
If you don't ask the person out, you'll never know, Diamond says.
"You'll end up obsessing, and that's worse than one minute of feeling bad," he says.