The Art of Woo: Six Ways to Win Over a Partner

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Let’s face it—dating someone new is tricky enough even when the tug of attraction is entirely mutual. Under the best of circumstances, the early stages of romance can feel like playing a game without knowing all the rules. That is doubly true if you have become genuinely interested while your potential partner seems undecided about whether to date at all, much less what sort of future you might share together.

If that describes you, don’t panic. The absence of a resounding “no” means that “yes” is still possible. Here are six sound strategies for tipping the romantic scale in your favor:

Check Your Motives. The most important step is to be sure you SHOULD try and win over someone who seems reluctant. Perhaps he or she is hesitant for a good reason: Maybe she is considering a move to another city, or he is still healing from a painful breakup, and so on. Upon reflection, you might realize you are more attracted by the challenge of winning her over than the prospect of a realistic and lasting romance. Be clear about why you want to pursue this person—and you’ll strengthen the relationship in the long run should you succeed.

Give It Time.  The seeds of romance germinate and grow at different rates for different people. Some, like green beans, shoot straight out of the ground as if spring-loaded. Others take their time and give the appearance that nothing is happening. This is the time to tread carefully. Romantic gardeners who give up too soon on the slow movers inadvertently kill what was almost ready to break through the surface. Of course, it is foolish to water bare ground forever; but if you’ve decided to woo someone whose feelings are slow to sprout, be patient.

Don’t abandon hope too soon. Provide Space. Einstein would agree that, even in this context, time and space are related but different. It’s possible to be realistic about the time it will take to see results and still crowd your potential lover with too much expectant hovering. The best approach is to relax, back off, and give the one you hope to love plenty of room to maneuver. You’ll know you’re succeeding when he or she begins to close the gap between you.

Pay Attention. There is nothing as attractive as being with someone who obviously thinks you are interesting. He really listens to what you say, rather than simply waiting for his next turn to speak. She asks intelligent and meaningful questions about who you are and what you think and feel. Thus, when pursuing someone who seems reluctant, use your time together wisely. Practice the art of awareness and alertness. In the process, you’ll create an irresistible romantic atmosphere. More important, you’ll fast track your reason for dating in the first place—to get to know him or her more intimately.

Employ “Smart Dating” Strategies. These days we are used to “smart” devices and applications that anticipate our needs and tailor content to our personal habits. But you don’t need to be a machine to know how this works, or to use it to your advantage. If you are trying to attract someone into a deeper relationship, why invite them on generic, off-the-shelf dates when you could choose outings perfectly suited to his or her tastes? Does she dream of going to Europe someday? Invite her to the travelogue documentary series at the public library. Is he a baseball fan? Get tickets to the game. You’ll demonstrate that you’re looking below the surface, and that you like what you see.

Give the Right Gift at the Right Time. Romantic gift-giving is an art form in itself. It isn’t easy to find the perfect balance between gifts that are over the top (Rolex watches and ski vacations) and under the radar (anything you grab at the supermarket checkout). But that sweet spot is defined by more than a gift’s price tag. It is about the romantic thoughtfulness you invested when picking it out. Once again, the more you know about the person you hope to attract, the easier it will be to choose a caring and meaningful gift—a new anthology by his favorite poet; the complete first season of her favorite TV show on DVD. Avoid the commonplace and mundane, if you want to awaken someone to your extraordinary romantic potential.

Remember: It isn’t about winning or losing, but how you play the game. Keep these tips in mind to play it well, no matter the outcome.

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