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1. Introduction

It's easy to feel shy about asking someone for a date, even when you're using an online personals service. Fear of rejection can be strong, and it's easy to talk yourself out of sending even a casual message. Fortunately, our dating experts are here to help! Follow these top tips and you'll be on your way to getting a date in no time.

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2. Be observant

Nothing's worse than an email with no relation to you or your profile. Generic phrases like "Your profile's cool, wanna chat?" will get you nowhere. Take the time to examine the profile—this means looking at something other than the picture—and pick out some features that make the person appeal to you. Then, write about those in your correspondence. Mentioning a shared interest not only shows that you actually looked at the person's profile, but it also sets up a topic for continued discussion—and a possible activity for a first date!

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3. Be funny

"Sense of humor" ranks high on everyone's list of desirable traits in a potential mate, but it's surprising how rarely people demonstrate this characteristic. Take the time to come up with a charming line that's tailored to the person you're writing. Try gently joking about a shared interest—"I'm glad to find out that another non-dork plays Dungeons and Dragons"—or bringing up a funny story from your past—"I see you're big on tennis. The last time I played, I got hit by the ball five times. Think you can help me improve?" Relate the joke to the other member's profile and you'll be getting a fun, flirty response in no time.

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4. Give a compliment

Flattery will get you everywhere, even with people who wouldn't admit it. "You're pretty" is a compliment, sure, but it's not a very memorable one. "Your lips are better than Angelina Jolie's," while not very likely to be true, is a much better and more specific compliment. And remember that compliments don't have to be based on appearance! Showing appreciation for a profile that's free of misspellings, grammatical mistakes, or punctuation errors is likely to get you points with the person who went to the trouble of creating a perfect self-description. Or, compliment the person on an unusual combination of characteristics: "I've never known any football players who also read Gore Vidal—how'd you get to be so unique?" Specificity is key, as is actually complimenting the person. (Hint: "You're better-looking than my ex" is not the right phrase for kicking off a new relationship.)

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5. Don't reveal too much

Telling your life story in your first email a) looks desperate and b) leaves you with nothing to talk about in subsequent communication. Mention a bit about your past and present—proving absolutely no information about yourself will seem strange—but keep it focused on the other person and on the future. You do want to provide your potential date with something to ask you about, but keeping it mysterious is guaranteed to be enticing.

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6. Ask questions

Not asking questions is like sentencing your email to be ignored. A well-phrased question or two provides the perfect provocation for a response from your potential mate. Don't get too personal, but don't be too generic, either. "What are you wearing?" paints you as a stalker, while "What's your favorite color?" is just plain dull. Strike a good balance between overbearing and boring by asking about favorite musicians or inquire why the person chose his or her career. Asking about things to do in the area is also a good way to set up a potential date. When you know what your love interest likes to do, you can suggest an activity that fits in with his or her interests.

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7. Follow up

Once you've crafted the perfect email, you're not off the hook. You'll have to wait for that response, then send another message if you want to keep the flirtation going. The way you respond depends largely on the other person's message. If you're getting the cold shoulder, say it's too bad the interest doesn't seem to be mutual, but invite the person to get in touch later if he or she would like. If your contact seems intrigued, respond soon enough to be remembered—but not so soon you seem desperate (answer 5 minutes later and you'll look like a stalker; 2 weeks later and you'll have been forgotten. When you write back, follow the suggestions above to kindle the spark between you!

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8. The Bottom Line

Remember, you're flirting, not looking desperate. The point is to make the other person interest in you. Avoid going on tirades, talking about exes, or revealing too much. Make yourself look good—but not perfect—and ask lots of questions. Yahoo! Personals, Matchmaker, Loveawake, and many other services offer instant messaging that's perfect for flirting. If the communication is going well, suggest an activity to do together for the first date. The response should be positive if you've been flirting successfully!

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