Romantic Encounter: How to Turn a 1st Date Into Something Wonderful

Make the effort to make a real connection—whether it's your first date or the 45th. (Fei Meng)

As Valentine’s Day approaches, here are some tips and techniques aimed at making a great connection on a first date—that work equally well for the 45th date, too.

Be Honest

When meeting someone new, there is no excuse to be anything other than 100 percent honest about your age, education, job, or family. Outright lies and half-truths have a way of rising to the surface sooner or later, and once exposed, there’s no way to go back and regain trust.

This requirement of being honest also applies to the chances of the relationship moving forward and evolving. First dates are intended to let each party learn about the other to see if there is interest in moving forward. If one or both sides don’t see a future, be honest so you both can move on.

Have Fun

You can’t connect with someone you can’t hear or see, making a movie a less-than-ideal choice for a first date. Choose a venue that allows you both to talk and laugh. If both parties are having fun, it’s more likely there will be a second date.

When making plans for a date, make an effort to discover what the other person enjoys, so you don’t bring them to a karaoke club when they would have really preferred going to the local art museum. During the date, pay attention to make sure they are enjoying themselves, so you can go to Plan B if needed. Oh, yeah—have a Plan B.

Pay Attention

It’s always tempting when meeting a new person to talk all about ourselves, but a better approach that makes a second date more likely is to sit back and allow them to talk. That doesn’t mean not saying anything, but rather refers to being a good listener, nodding, and commenting to keep the conversation going.

Resist the urge to one-up their stories with one of your own—that will simply let them know you were only waiting for a chance to take over the conversation rather than actively listening to them and having fun. Sometimes, people blather on because they are nervous, so smile and maintain eye contact to put them at ease.

Dress Smart

We’ve all seen couples that were clearly on their first—and last—date. One of them will be dressed very nicely, while the other will look like they slept in their outfit—for several days, and clearly has no idea of how to use a hairbrush or the basics of grooming.

Dressing provocatively sends the wrong signals, so leave the latex in the closet. Dressing the way you normally do lets them develop a better feel for you, which is to say don’t dress like an outlaw biker if you are a banker who can’t even ride a Huffy.

Be Thoughtful

Be on time: 7 p.m. does not mean 7:30, and it definitely doesn’t mean 8 p.m. If you realize you are running late, let them know as soon as possible, giving an honest reason and an adjusted arrival date. But don’t do this more than twice, or you won’t get more chances.

Far too many first dates are ruined because one of the parties can’t resist talking about how an ex, or all of them, wronged them. On a somewhat related note, even if the most beautiful person in the world walks past, banging a drum and playing the trumpet, do not under any circumstances get caught looking.