Romantic admirers may stare wistfully from afar, indulging the fantasy of swooping in and dazzling the object of their affections with their social prowess. However, nerves and awkwardness often accompany feelings of attraction, stifling opportunities before they start. Have a clear but flexible conversation plan in place before approaching your target to boost your own confidence. A bright smile, clear eye contact and a self-assured air are as important as the words you choose.
Compliments
To begin a conversation on a positive note, open with a compliment. Avoid cliched compliments about someone's eyes or smile. Instead, choose something unique that could launch the conversation in a new direction. Both appearances and behavior, such as public speaking skill or posture, can spur a compliment. Be genuine and express your true feelings when you give a compliment, as people can easily detect insincerity. Avoid excessively personal or physical compliments. Even if you think a feature looks unique and interesting, avoid calling attention to physical flaws that the listener might be sensitive about.
Open-Ended Questions
Asking questions engages your conversation partner while conveying your interest and attention. Closed questions can be answered easily with a single word, while open-ended questions often lead to longer discussions. Start a conversation with lighthearted, funny or hypothetical questions, such as "If you were stuck on a desert island, what three things would you bring?" Using hypothetical situations allows you to approach intimate and personal topics without an excessively political or prying stance. Be careful not to pepper your conversation partner with questions. If his answers to open-ended questions are terse and guarded, this is a clear sign he wants you to back off.
Storytelling
Volunteering stories is a quick way to make a conversation more intimate without forcing the other person to divulge information. Tell short or moderate-length stories about funny occurrences, interesting events or observations. Be sure you remember the story well from beginning to end. Add in enough detail so your listener can follow the story and jump in with questions or tangents. You don't have to choose the funniest thing that ever happened to you -- an interesting event from the past week or two is sufficient. Excessively negative or obscene stories may turn off your listener. If you are willing to make yourself vulnerable, divulge an embarrassing incident that will get laughs and sympathy.
Jokes
People are attracted to folks that make them laugh. A good joke can set a positive tone for a conversation while showing off your cleverness and sense of humor. Pick one-liners or short jokes that segue naturally into discussion. Observational or situational humor creates a sense of camaraderie that makes continuing the conversation easier. As with stories, be sure of your audience's reaction before opening with a crude or controversial joke. Avoid put-downs or criticisms, which put a negative spin on the conversation.
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