Advice

How many times have you walked into a bar or restaurant and approached an attractive woman? And how did it go? What do you think helps to engage a woman in conversation, or more importantly, to spark her interest in you?

Much like approaching a total stranger, online dating profiles are a way to make the first move - to reach out and introduce yourself to someone. The key is to put some time, thought, and effort into it, much like you would in person. You won't attract someone if you rely on the same old clichés. It's important to be yourself, have fun, and try to strike up a conversation. The key is engaging her.

Following are some clichés you should avoid adding to those profiles:

"I love to laugh" or "I have a good sense of humor." Who doesn't? Instead of stating the obvious, express yourself. What exactly makes you laugh? If you tell jokes, then tell a joke. Let your own style come forward here.

"I'm happy to go out or stay in," or "I'm just as comfortable in a jacket or in jeans." Again, what does this say about you? Instead of trying to be everything to every woman, state exactly what you do like doing on the weekend - even if it's just walking your dog and grabbing a coffee in the morning. Be yourself.

"I don't want drama." Have you moved on from your past relationships? Because this sounds like you're still angry or resentful, which isn't going to attract a great woman to you. Women generally don't like drama, either.

"Looking for something casual but am open to something long-term." This is just evasive. Make up your mind and stick to it, whether you're looking for something long-term or just to have a little fun.

"I'm living life to the fullest." Yawn. What does this mean? Explain how you live a full life - do you wake up every morning at 5am to go running, close at least one business deal a day, or go on vacation at least five times a year? Living a full life means different things to different people - explain what it means to you.

"I like going to bars/ going to Vegas/ taking road trips." While this is great, you and a million other guys all said the same thing. Again, it's important to get specific. Talk about the trip you loved the most and why.

"I work hard and play hard." We get it. You work long hours and you drink with the boys. But what does this mean for the women you date? Instead, I recommend you let women know how you see spending an evening with them instead - how they fit into this picture. In other words, get creative and describe your ideal date. (And leave work out of it.)

Sometimes communicating with someone via the Internet can feel like a labyrinth. On the one hand, you have the ability to edit what you say, take back that awkward joke before you send it. You can think about a response for hours as you figure out what you want to say, and it’s not too unusual because hey, people have busy lives.

On the other hand, you don’t get all those additional clues and context. You don’t get the tone of voice, the body language, the gestures, the funny faces. Whereas in person, a sentence would slide past you and you’d only think of it later if you remembered it, in an email every single sentence can get analyzed and reanalyzed. What did this person really mean? Was that “ha ha” genuinely full of mirth or sarcasm?

It can feel like you’re typing in a code - when you’ve only got a partial key to solving it. What many people don’t realize, however, is that you don’t have to. Instead of having a conversation in a language you only partially understand, you can always do what many people feel they can’t: ask questions, clarify, and be straightforward.

“Look at this email,” a friend said to me. “I can’t tell if she’s saying she is ready to meet in person for a date or that she’s not ready, and won’t be for some time.”

“I would interpret that as that she is ready,” I replied, “although I can see where this phrase is a little confusing.”

“Hmm,” he said, frowning, “I’m not convinced.”

“Only one way to find out,” I said. “Ask her if she’s ready to meet in person, for something small like coffee.”

He gaped at me. “Isn’t that a little forward? What if she isn’t ready?”

“If she’s not ready, she’ll tell you,” I said. “You’ll have the answer to your question, and you’ll be able to properly decide if you want to continue emailing or if you want to move on. If she is ready, she’ll tell you, and you’ll meet in person. Either way, she knows you’d like to meet, and you’ll both have more information than you do right now.”

What my friend did not realize was that asking a simple question, one that clarifies something you’re uncertain about, is not impertinent or dumb. It shouldn’t make anyone think less of you (and if it does, chances are they aren’t the sort of person you want anyway). It never hurts to make sure you’re on the same page - and if your communication feels really muddled, chances are your date is confused too.

Being honest when you don’t fully understand what’s going on also lays a great foundation for communication. If you’re not afraid to clarify, you’ll be more willing to discuss trickier issues later; it won’t be as uncomfortable or awkward.

Emailing might feel like you’re wandering in a maze wearing earmuffs and a hat that obscures your vision - but it doesn’t have to. And you don’t even have to email, if it comes to that; phone, video chat and meeting in person are even better. Don’t be afraid to actively make your communication clearer; you’re just making it easier to feel out your potential chemistry, and lay the foundations of a better relationship.

One of the most overlooked aspects of successful online dating is knowing how to attract people to you online. After all, this is your first chance to make a good impression - and it starts with crafting an intriguing profile, one that makes people want to engage with you.

Think of it this way: if you were to approach an attractive stranger, you want to have a great opening line, as opposed to something that sounds like a cliché (i.e. "Hey, come here often?"). You want to strike up a conversation, to spark his interest.

Which is why it's important to put a little work into your profile. It helps to be specific about your experiences, to let your matches get a picture of who you are. When you're too generic in your description, there's nothing that makes you stand out.

Following are some clichés to avoid - be sure to change them now!

"Family and friends are really important to me." While this might be true, it doesn't say anything about you. Try telling a story instead: "I love playing basketball with my adorable twelve-year-old brother every weekend."

"I love to laugh/ have fun, so a sense of humor is a must." And who doesn't? Everyone thinks they have a good sense of humor. Instead of saying this, describe something that makes you laugh, or the best outing you had in the past couple of months.

"I never thought I'd be doing this online dating thing..." If you're admitting this to online daters, you're not going to get very far. Even if this is true, don't say it. It's insulting to everyone else.

"I'm looking for someone taller than me, at least six feet." It's good to have some physical preferences, but if you limit yourself to a specific group of men, you're going to restrict your choices. Also, other men (who are six feet) might think you're too picky. Be more open.

"Looking for my Prince Charming/ Knight in shining armor/ etc." Can you imagine saying this in person to a total stranger? Then don't say it online either. No man wants to live up to that. Relationships take two people, not one savior. Instead, focus on what you want from a real relationship with a real person.

"Don't contact me if you're a player or a cheater." Nobody wants to date someone who hasn't forgiven a past transgression. And don't assume future boyfriends are out to get you. Start on a clean slate, and you'll get more responses.

"I like all kinds of music/ movies/ video games/ etc." Nobody likes everything, and most people have a preference. Don't be afraid of stating yours. It sets you apart from others, and you can feel free to be yourself.

What do you do when you're 30, newly single, and totally over playing the field? If you're Amy Webb, digital media consultant and author of Data, A Love Story: How I Gamed Online Dating to Meet My Match, you decide to hack online dating.

After enduring a handful of disappointing dates, Webb knew she needed to rethink her approach to dating online. She turned to her background in data analysis to figure out exactly why her profile was attracting the wrong kind of man.

Webb began by listing the 72 different attributes she required in a partner. Some were obvious: he had to be smart and fun. Others were more specific: he had to share her appreciation for spreadsheets and be willing to listen to George Michael. When the list was completed, Webb broke her dealbreakers into a system of tiers. At the top were most important characteristics, ranked from 1-10. The result was a 1000-point scale that she could use to evaluate and categorize the men she dated.

For many of us, that's already thought and effort above and beyond the call of duty. But Webb didn't stop there. Before putting together her optimized profile, she set out to see things from the other side.

Posing as each of 10 male archetypes, Webb created profiles on JDate and spent the next month testing the online dating waters as a man. She studied the behaviors and habits of women on the site, collecting data like language used and number of hours elapsed before responding to a message.

"When I saw what was there, I was mortified and humiliated," Webb says. "I knew how bad my profile was, and what damage I'd done to myself because of what I posted. I had essentially copied and pasted my resumé."

She also discovered that the type of women her dream men were attracting fit a profile:

• Their pictures showed some skin.
• Their bios were short and optimistic.
• They waited 22-23 hours before responding to messages.

Armed with her new knowledge, Webb revamped her profile and woke up to 14 new messages and 68 views overnight. "Within a few days I was the most popular profile on the site. It was like I was the prom queen of JDate," she jokes. "I've never been that popular before. I probably never will be again."

Maybe not, but it doesn't matter anymore. She found her happy ending online, a man named Brian who became her last first date.

Are you returning to the dating scene after a divorce or the end of a relationship, uncertain of who might find you attractive since you're no longer 25 years old? Rest assured, you have nothing to worry about.

Baby boomers are the largest population in the US, and many are single and looking to date. If you are among them, you're in good company! Don't let age be a factor in keeping you from pursuing love. It can be found at any age.

In fact, as you get older, you're more apt to have learned a thing or two along the way and are able to make better choices. (And you'll have more fun meeting people, without all the pressure of finding "the one.") Twenty-somethings might have youth on their side, but they have a long way to go in learning what they want and need in a relationship.

That said, here are some advantages to being (and dating) a baby boomer:

You can afford a nice date. Dinner at a five-star restaurant-why not? This doesn't happen with the twenty-something crowd. They prefer coffee or grabbing a drink at a bar, or something equally casual and inexpensive. But you are able to be a little more romantic and generous, so go with it! Splurge on a weekend getaway if you desire.

You have established yourself. You're not struggling to make a name for yourself in your career anymore, unless you want to try something new. Work isn't the only topic of conversation, and your career is only part of who you are. You realize that there's more to life than work, and you want to enjoy it. So take advantage and talk about other things - your passions, where you've traveled, what else you want to do.

You have good stories. With time on your side, you definitely have the advantage of experience. You've gotten more interesting as the years have progressed, because of the events in your life, trips you've taken, professional risks you've taken on. Share them with your dates, and let them share with you.

You know who you are. This goes with what I've been saying. You're not looking to impress anyone, you're more comfortable in your own skin. There's nothing more attractive to your dates than confidence.

You know what you want. Knowing what you want saves a lot of time and heartache, whether you want a long-term relationship or not. You know when to walk away from a relationship that isn't working, and you know when someone great is sitting right across from you.

It’s not unusual to hear about outside pressure when it comes to dating - well-meaning friends and family who attempt to push you in the direction of one person or another, or who encourage you to date someone in whom you’re not all that interested. However, what you might not know is that it’s also common for the pressure to come from another source: yourself.

When you have that “spark” on a first date and your date is clearly feeling it as well, deciding on a second date is a no-brainer. But what about when the date isn’t particularly hot, but they’re not unattractive either? What about when there’s nothing “wrong” with them that you can pinpoint at all, even if you’re not sure you’re feeling it? What about when the two of you are completely compatible on paper? And what if your date seems interested in you?

That’s when the self-pressure comes in - those voices of fear that tell you this person may be your best, or only, shot at love. Or maybe you’re waiting for an excuse to call things off, but you don’t see anything particularly offensive... so you just keep going on dates because you think ending a relationship without an obvious reason is cruel.

The truth is, prolonging a relationship you’re not enjoying is actually what’s cruel. While rejection stings, it’s better to be free to continue the search than to waste time on a relationship that ultimately goes nowhere. And you’re doing as much as disservice to yourself as to your date.

“But wait,” you might be thinking. “Surely there are some people who need that extra time to really make a decision. Or maybe they have impossible standards to begin with and they never give anyone a chance.” That’s certainly true, and you find that, over time, no one “measures up” to your dream date, it’s worth exploring the possibility that the problem lies elsewhere. However, that doesn’t change the fact that whatever the underlying cause, you’re not doing your date any favors by prolonging the doomed relationship. If you have impossible standards, it’s up to you to work on them and change them, not a random date.

You don’t have to make a snap decision about a potential relationship, particularly if you know you tend to need a little extra time when it comes to big decisions. And sometimes relationships naturally start with a slow burn, while others begin strong and flame out fast. Only you will know what works for you and your date. But if it’s fear that’s keeping you from moving on, you’re probably not indecisive for the right reasons. There’s always the possibility of love out there; don’t let fear hold you back and impair your judgement.