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How To Ace First Dates


If you’re returning to the dating scene, read this advice from a love expert on how to guarantee date #2.

By Chelsea Kaplan

f you’ve recently returned to the dating scene after the end of a relationship, your confidence may not be at an all-time high. If you could use a pick-me-up, not to mention a few tips on how to date better, let us help. We chatted with love expert Victorya Michaels Rogers, author of The Automatic Second Date: Everything to Do and Say on a First Date to Guarantee a Second. Here, her advice on how to make a successful, self-assured return to the dating pool.


Let’s say a person is back on the dating scene after divorce or loss of a spouse—how can he or she adopt a positive, hopeful attitude?

Before you jump back into the world of dating — especially after a long absence — take time to evaluate where you’ve been and where you want
Laugh at your date’s jokes—he or she will be putty in your hands!
to go. You’ve just experienced a painful season to say the least, so allow yourself time to heal as you deliberately reflect back and look forward. It’s time to love yourself first and deliberately pursue the life you always wanted!

What are some good first steps?

Pull out a journal and reflect back on what you loved and what you hated about your love life thus far. For each previous relationship, devote one piece of paper to listing your former partner’s good qualities (on the right side of the page) and his or her bad qualities (on the left).

How can this exercise help someone move forward toward finding love again?

Making these lists can help you try to visualize the love you hope to find in your future; you vow to avoid re-experiencing the bad treatment you’ve received in the past, while at the same time you affirm to repeat the good. Reviewing these lists can help you compose a new list describing your ideal relationship—and by that I don’t mean “someone who will ask me out.” I’m talking about a list of what you specifically want to find in a companion. Reverse the negative qualities you’ve attracted in the past and copy the good you want to repeat, and write down everything else you can think of that would just be wonderful to find in your new mate. Be as detailed as possible so you can visualize this person, keep this precious list nearby, and review it often as you jump back into the world of dating.

In your opinion, what are the best places to meet other singles who have recently returned to the dating scene?

I advise skipping bars and clubs and just plunging yourself into the social world around you—be it at your church, country club, charity, or a special-interest group at your community center. As you interact with more and more people, you will automatically find yourself around — and introduced to — available men and women.

Can you share with us some definite “do’s” to keep in mind when on a date?

In addition to looking and acting your best (this means adopting a
Plunge yourself into the social world around you.
positive attitude and exhibiting good manners), I always recommend asking your dates lots of questions about themselves. It’s their favorite topic, and you want to know the information anyway!

Any specific dating tips for women?

Laugh at his jokes; he will be putty in your hands. Also, I advise flattering him genuinely and specifically—men eat up admiration. When you talk, look him in the eye. Finding someone to actually look at and listen to you is a rare treat for most men; if you do this, you will definitely be remembered. Lastly, have several girlfriends in your life to share your dating life with. Better to talk endlessly to your girlfriend than scare your new man away with too much girl talk.

What about advice for men?

Guys, you may be excited to begin your romantic life again, but pay attention to any red flags—you’re old enough to pay attention to blatant warning signs! Take it slow, even if she wants to rush the relationship. Men tend to get scared and run away when it’s too much too soon, so take your time and slow things down if you need to—as you move forward at a comfortable pace, you may find you have the real thing.

If someone wants to guarantee he or she will get asked out again, what tips would you offer?

Getting to know each other, enjoying laughter and being comfortable is the goal for not only having a successful first date, but also to ensuring a second. If you are really interested in your date, offer your undivided attention. Make eye contact, ask questions, and if he or she tells a joke, laugh! Mirror your date’s tone, mood, pace, and even the position in which he or she sits. This body-language exercise is so subtle that your date probably won’t notice, but he or she will be comfortable with you and want to see you again.

Are there any behaviors to avoid—things that can get in the way of your getting asked out again?

I definitely recommend that you avoid having sex on a first date. The transition from being married and freely having sex with your spouse to holding back your passion as you jump back into the dating arena can be difficult for some people. But if you want a relationship to develop, you must have restraint! Getting that second date is about holding back, not putting out. The physical always progresses, so take it slow so you have somewhere to go.

What would you say to someone who went on a date, thought everything went beautifully, yet never received a call back for a second date?

If you haven’t heard back from your date within a couple of weeks, even if you were convinced it went wonderfully, think back about that evening. Did you really have anything in common? Did you talk too much about yourself? Did you “go too far” physically to the extent that you felt a little guilty the next day? Might you have acted too needy, too pushy, too bossy, too snotty or too boring? If any of this is the case, your date may have been scared away and wouldn’t tell you even if you asked. Don’t be too hard on yourself, though; let it go. It was only one date and if he or she’s gone, that person wasn’t meant for you. At least by reviewing it honestly in your mind, you may be able to learn what not to do the next time and move closer to find someone you click with.


Chelsea Kaplan regularly appears as a guest on XM Radio’s “Broadminded.” Her blog, “I’m Somebody’s Mother?” can be found at www.chelseakaplan.com.
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