When you’ve established rapport with someone, it becomes easier for you to figure out the right thing to say. You’re aware of what’s happening in his or her life, what to talk about, and when he or she would appreciate a cheerful, private talk with you.
Watch out for any appropriate opportunity to ask them out. You can start small, by asking him or her out for coffee. A coffee shop is a very casual, relaxing place to just get to know each other. It’s also the most tactful transition from investigative flirting to dating. You can talk about anything over coffee, without having to look like you’re already dating. After coffee, you can further determine if this is a person you would like to continue seeing in a more romantic fashion.
Never commit to anything immediately after the first “coffee meeting”. You need time to reflect on whether a lunch or dinner date would be appropriate. Take a few more coffee meetings with this person if you must, if you’re unsure.
Another tactful way of making the transition is to go on group dates. It doesn’t even have to be an overtly considered group date—just a group of friends going out to have a great time. It’s a good way to get to know the person you’re attracted to better, without you having to look more forward than you want to. Having friends around (both male and female) also protect both you and your prospective date from potential embarrassment, especially if either of you suddenly realize you aren’t that attracted to one another. There’s no unspoken
commitment to see each other again on a one-on-one basis.
Group dates can still feel awkward, however. You have to make sure it’s a group you’re comfortable with, and you’ll have to take into consideration everyone’s preferences throughout the time you spend together. Plus, the older you are, the less likely you are to like group dates (it may start looking like an adolescent approach to you).
Once you’re sure your timing is right, choose an appropriate situation to ask him or her out for a one-on-one lunch or dinner. Take the plunge and ask him or her out!
Rule 2. Be confident, creative and thoughtful in arranging your dates.
Being confident when asking someone out on an all-out date means you have the courage to do so. Courage is the strength to do what needs to be done, even if you have the fear of failure lurking around in the back of your mind. Be confident, have courage! You have come this far, and have expanded your horizons. You have much to offer others as a human being, and you can really tell when someone likes you back, enough to go out on a real date with you—so go ask!
Remember, though, to arrange your date creatively and thoughtfully. What does this mean? Before you ask someone out for a date for the first time, think deeply who that person is, and what he or she would appreciate experiencing. Consider what his or her interests are. What would truly make them
smile, make their eyes dance? For your first real date, where should you go and what should your main activities be?
(Be realistic—don’t arrange for a date that will cost you more than you can afford. That’s why I emphasize creativity here. If your prospective date is the type of person who tends to find something “romantic” the more expensive it is, I strongly suggest re-thinking your prospects!)
To get you inspired, here are some real-life dating activities some people have tried. Some are classic dates, while some are offbeat and budget-friendly!
• A movie or a baseball game, then sandwiches at the best
Italian deli nearby
• A home-assembled gourmet picnic-lunch at the nearby park, complete with wine or champagne
• A rock concert, a musical or opera, then dinner
• Spend one whole day, fishing
• Spend an afternoon at the circus, fair, or amusement park; ride all the rides like children, and eat some of the same kiddie stuff (e.g. cotton candy, fritters, popcorn, etc.)
• Walk through the entire art museum, then have lunch or dinner
• Watch stand-up comedians at a comedy club
• Visit the aviary, zoo, safari or botanical garden.
• Take a horse-drawn carriage ride before or after dinner.
• Teach your date (or be taught) how to skate.
• Go on a hot-air balloon ride over the countryside or a national park.
• Dress up for Halloween or Christmas, and bring gifts to the elderly or orphaned children
• Karaoke night—just the two of you
• Visit the flea market and see if either of you can find the cheapest, best find (e.g. books, vintage photos, furniture)—then have lunch
• Lunch, then an afternoon at the beach to swim or build sandcastles
• Go to a masked or costumed ball (in period costume)
• Hang out at a science convention or comic-conference;
make sure to bring your cameras and/or be in costume.
• A game of tennis, squash, badminton, or any other one-on- one sport in the morning (then head home for a quick shower), then meeting up again for lunch
• Bake a cake or bread at home or at a weekend culinary class, to make food you’ll share for the rest of the week
• On a clear moonless night, go star-gazing—if both of you are even mildly into astronomy and you have a telescope, even better
If you doubt the effectiveness of going on a creative first date, then you’re missing out on the opportunity to hook someone’s heart completely, in an elegant or subtle way. You’ll
even make a lasting impression, one that will stay for an entire lifetime.
Nancy, a 30-something year old mother of two, fondly remembers when she first went out on a date with her husband Avery. “It was Labor Day weekend,” she said, “And he invited me to go out with him to the nearby nursing home. Labor Day weekend, everybody’s out partying with their family, friends and lovers, and here he was, asking me to go out on a date with him at the nursing home!”
But she went anyway, and got the surprise of her life. She learned that Avery played the piano, and he was to play an hour or two for the old folks at the home that day.
“He was brilliant on the piano, and as I watched him from the side, he kept looking my way and