How to Make Conversation With a Man Online

Online dating is a popular way of meeting eligible men.Online dating is a popular way of meeting eligible men.

Many women are turning to online dating in order to meet a potential mate. After you set up your profile, write a killer headline that will attract men, and post your best photos, you’ll have to actually have conversations with your admirers. Whether you’re emailing, chatting live or spending time in a chat room, mastering the art of starting and carrying on a conversation is imperative.

Step 1

Ask him questions about himself and his life. People like to talk about themselves more than they like to listen. He’ll feel closer to you once he imparts personal information. Ask him about his family, career and favorite travel destinations, for starters. Pay attention to his answers, and use them as a springboard for developing more conversation.

Step 2

Flirt lightly, but don’t go overboard. Being playfully and slightly flirtatious is fine. When you cross over into heavy flirting, though, the guy may get the wrong impression. Unless you want him to think that all you’re interested in is a quick fling or physical relationship, tone down the flirting a bit. Remember, online conversations sound a bit harsher by nature than they would in public, since you’re missing tone and body language.

Step 3

Be honest. Don’t lie about your education, age, height or anything else that the man you’re chatting with may ask you. If you truly don’t feel comfortable answering a certain question, say so honestly. Not everyone is upfront about their past relationships or income. It takes time to form a connection and share this information. There’s nothing wrong with setting personal boundaries in the beginning.

Step 4

Pay attention to your grammar, spelling and punctuation. While there’s plenty of leeway when writing online, especially when you want to type quickly to keep a conversation going, you don’t have to sacrifice coming off as uneducated. Poor spelling and grammar can be a turn-off to an educated man. If you’re unsure of how to spell a word, look it up quickly before hitting “Send.”

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  • Try to stay up on current events so you will have plenty of fresh topics to discuss.


  • Safety is a big issue when it comes to online dating. Protect your identity as much as possible. Even if your photo is available for viewing, you don’t have to post your last name, address or personal email address. You can create an entirely new email address to be used with your online dating profiles. Be careful about revealing private information, like your place of work or details about your family.

About the Author

As a full-time writer in New York's Hudson Valley, Lindsay Pietroluongo's nightlife column and photos have appeared regularly in the "Poughkeepsie Journal" since 2007. Additional publications include "Chronogram," the "New Paltz Sojourn," "About Town" newspaper and "Outsider" magazine. Pietroluongo graduated from Marist College with a B.A. in English.

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