Dating 101

Dear Digital Romeo: How Do I Seduce a Guy Through Chat?


Digital Romeo is an advice column about socializing and finding love online at If you have a question, email us at [email protected].

"Dear Digital Romeo,

I never know how to start conversations with guys online. It's awkward just saying 'Hello,' and where do you go once the guy says 'Hi' back? I also have a hard time telling if a guy's interested. Can you help me?"

Online flirting can be difficult. Sure, it gives you the time look over someone's profile and formulate a good response, but it's hard to start a conversation and gain someone's interest when they're not even physically there.

It's important to remember that online flirting is meant to be casual and fun. Yes, words are important and chat can lead to the beginning of a relationship. But at the outset, it should be playful and engaging. Just like in real life, it pays to be charming, attentive and personable.

Here are a few tips to help you break the ice:


Unless you're just cruising for a quickie, starting a conversation with "Sup?" — or worse "Stats?" or "Pics?" — will go nowhere, especially since most people's profiles have their general stats and pics already on display.

If you're one of those guys who sends out a general impersonal message like "Hey, I'm new to the area and am just looking to make friends" to lots of guys at random, you should know that most guys consider that a form of spam and hardly ever answer. In fact, I tend to block those guys because... hello? I don't want to chat with a spambot.

A simple "Hey" or "How's it goin'?" comes across as much friendlier and more conversational. And if you're looking to flirt right off the bat, "Hey, handsome" or "Hey there, tiger" will make your interest pretty clear.


A much better way to garner interest after the initial hello is to read a person's profile and then ask them questions based on what you find. For example, if they're into arts, ask them if they like a favorite artist of yours. If they like cooking, say, "Me too. What's your speciality?" If they're into movies or music, ask what kind.

Asking personal questions shows that you're paying attention and are interested in learning more about them on a more intimate level — it's flattering, flirtatious, and shows intellectual maturity. It also helps if you ask questions about similar interests so that you'll have opinions of your own to throw into the conversation.

Just make sure to keep the conversation light at first and not to dominate it with questions or lots and lots of blather. No one likes a nervous windbag, and there will be time to discuss more personal matters after you get to know each other first.


Though we're told to distrust flattery, there's nothing wrong with complimenting a person's looks or interests — just as long as the compliment comes from a place of sincerity. For example, if a guy's blowing you away with his pics, just say, "Hey, I love your pics." It may sound dumb, but it's actually a good, straightforward way to compliment their attractiveness and whatever they're doing in said pics.

An even better move is to compliment them for something personal they've included on their profile. If you see they speak three languages, say, "You speak three languages? That's awesome!" and follow up with a question like "How did you pick those up?" or with some humor like "I only speak two: English and Pig Latin."

If they tell you they play tennis, you can say, "I bet you have a killer serve" as way to praise their athleticism. If they're from a part of the U.S. that you like, give a specific compliment about it ("Oh, I hear winters there are fantastic.") If their job sounds interesting, say so and ask questions about its most intriguing aspects. If you're feeling really bold, pay them a sexual compliment ("I bet you look great in a leather harness") or the trustworthy "How in the world are you single?"

A word of warning: A little bit of flattery goes a long way, so use it sparingly. If you try to butter them up too much, your flattery will come off false — or worse, desperate.


Online dating doesn't need to be so serious or consequential. Yes, you're looking to meet people and go on a date, but that doesn't mean every interaction has to teeter between full-on acceptance or flat-out rejection.

On the contrary, this is an opportunity to explore and banter with other guys — to try on different aspects of your self and to see what works and what doesn't.

Feel like being flirty? Try some come-on lines. Feel like being dirty? Try some sexy talk. Wanna sound intellectual? Mention the books you're reading. Wanna sound weird? Make a non-sequitur comment about baby penguins. Wanna seem wild? Mention how much you'd love to go hang gliding in body paint while listening to hair-metal. Playfulness is important because it's the best way to convey the person behind the profile. You may have great pics, a well-written self-introduction, or a bunch of exciting interests on your profile, but chat is your place to show just how fun and engaging you really are.

Experimenting on chat is especially fun when you've found a guy you're OK just chatting with. That way, you can test out different things and save your best conversational skills for a guy you really like. If it goes south, there are plenty of other guys to chat with.

Also, there's no need to fire off responses ASAP. Give your words a little thought and keep them fun. No one ever died waiting for a chat response.


When we chat, we usually assume that the person on the other end has as much time as we do; but that's not always the case. Instead of wondering if a guy's interested, here are ways you can gauge his interest:

- How quickly he responds

- Whether he asks any questions about you

- How directly he responds to your questions about him

- The amount of personal details he provides

- His level of flirtation, attention to profile details, and general playfulness

Remember, if he's providing brief responses or taking a very long time to answer back, he could just be busy or disinterested. Whatever you do, don't get impatient or offended. Often people will chat while they're watching TV, working or doing chores. If a chat ends suddenly, accept that the guy may be tied up and just hit him up later rather than pressuring him for an immediate response.


Some guys are just interested in just chat. But at some point, most will want the online flirting to eventually move offline into the real world. Before you meet your handsome stranger in person, it's important to establish a good connection.

Some guys transition from chatting to offline interaction by first trading phone numbers or becoming friends on Facebook so that you can take a closer look at their friends, their social habits, and feel them out a bit more before committing to a face-to-face interaction — and both of these are good ideas.

But if you've already made sure that the person is sane and you're serious about meeting, suggest a specific time and place. Saying, "Wanna go out for a drink Friday evening at Moby Dick's?" is a lot better than leaving it at "Hey, wanna hang out sometime?" Specifics show that you have a plan and are confident about creating some time together.

These are just a few tips for getting a conversation going, but you should also read this great article about safe online chatting to learn more great ways to safeguard yourself against any online ne'er-do-wells.

On the whole, most guys are just looking for an interaction with a genuine person, whether for good conversation or to meet up for fun. Playful engagement is the key and will get you where you wanna go, no matter your destination.

Got suggestions or questions? Share them below in the comments section or email us at [email protected]. See you online!

Tags: DATING 101