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Trying to start a conversation with anyone can be daunting, especially if it's on a social media platform like Facebook. On Facebook, you don't just run into people or notice someone across the room, unless you're active in groups. However, you can start a conversation with a guy, especially if you first notice him in a group. Whether you're trying to win a date, a new friend, or a business connection, this article will help you get started.

Method 1
Method 1 of 4:

Starting a Conversation with a Guy to Date Him

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  1. See what common interests you have before initiating a conversation, so you have something to talk about. [1] If most of his profile is set to private, you can ask him about his favorite movie or book to help get the conversation started. [2]
    • For instance, you could say, "I see your profile is set to private, so I'm curious why you're hiding your favorite book from people. What do you like to read?"
    • Reader Poll: We asked 267 wikiHow readers how they initiate a conversation with a guy online, and 48% said talk about something on his profile. [Take Poll]
  2. Most people are willing to chat for a few minutes if you need some help. So ask for help with a problem you're having. If you don't actually have one, you could ask something about Facebook, such as the following: "I can never figure out how to break up my paragraphs in a post without making the post send. Do you know how to do that?" [3]
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  3. If you're new to the area (or even if you're not), try asking him for restaurant recommendations as a way to open up the conversation. [4]
    • Try asking a question such as "Hi, I'm new to the area. Can you recommend any good Japanese or Thai places in the area?" If he says yes, ask him if he'd be willing to meet you at one.
  4. That is, ask him if you've met him before. You can mention a place you go often. He'll say "no," but you can move on from there. [5]
    • For instance, you could say, "Have I met you before? You look so familiar. Do you go the Panera Bread on 10th Street?"
  5. People love to laugh, so you can draw him in by making him laugh. The best jokes are ones that will connect you. [6]
    • If you see he likes the same sports team as you, you could make a joke about how bad the team is doing, such as "I noticed you liked our local baseball team. They're doing so bad this year, I think my kid's little league team could beat them."
  6. People like to hear good things about themselves. Pick something you notice on his profile. [7] It can be about his appearance, but it doesn't have to be. In fact, studies show that compliments not focused on appearance work best.
    • You could comment on his taste in books: "You have great tastes in books! I loved The Ocean at the End of the Lane, too."
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Method 2
Method 2 of 4:

Starting a Conversation to Become Friends

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  1. Like starting a conversation for dating, you should always check out his profile for common ground, even if you're trying to become friends. If it doesn't have public information, ask him about it. [8]
  2. If you just want a friend, you don't want to send a signal that you want something more. [9]
    • In other words, don't flirt. You don't want to comment it on his cute eyes if you just want to be friends.
  3. Say why you're contacting the person and what you want: "Hi, my name is Jake, and I'm looking for new friends in the area." [10]
  4. People like to talk about themselves, so ask him about what he likes and who he is. [11]
    • As an example, you could say, "Hi, I noticed your profile today, and I found it interesting. Can you tell me more about yourself?"
  5. When beginning a conversation, open-ended questions (questions that require more than a "yes" or "no" to answer) encourage the conversation to continue. [12]
    • For example, instead of asking "Do you like books?" ask him "What kind of books do you like to read?"
  6. For instance, if you both like basketball, focus on that. [13]
    • For instance, you could say, "Hi, I'm Ashley. I see you love playing basketball. I love to shoot hoops, too. Did you play for your high school or college team?"
  7. That is, use "howdy" or "what's up?" as opposed to "hi" or "hello." Studies done by OkCupid show a person is more likely to respond to an unusual word.
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Method 3
Method 3 of 4:

Starting a Conversation for Networking Purposes

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  1. It's always important to have as many details as you can before starting a conversation with someone you don't know well. See where he works, what he does for a living, and where he lives. You can also look for common ground, such as similar interests or the fact that you both have two cats. [14]
  2. That is, if you are contacting person because he's a friend of a friend or because someone he knows recommended you chat, bring it up. [15]
    • As an example, you could say, "I'm writing to you because Jeff Grace of ABC Financials suggested I get in touch with you."
  3. If you notice the person works in a similar field, ask about the job he does. [16]
    • For instance, you could say, "Hi, I'm Jess. I notice you also work in engineering. I'm new to the field, so I was wondering if I could ask you some questions about your job."
  4. That is, tie in your location to initiate the conversation. [17]
    • You could say, "Hi, I'm Beca. I'm new in Phoenix, and I was wondering if you have some time to talk about jobs in computer science in this area."
  5. If you're looking to make connections, mention that. If you're trying to find places that are hiring, ask about that. Most people are willing to help if you state what you want. [18]
    • For example, you could say, "Hi, I'm new to the area, and I'm looking to make professional connections in my field. Do you mind chatting with me for a few minutes?"
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Method 4
Method 4 of 4:

Being Considerate

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  1. That is, make sure you're not interrupting anything. People may respond to you but not really have time for a drawn-out chat. [19]
  2. If the person makes it clear that he doesn't want to chat now, ask if you can chat in the future. If he says no, respect his wishes.
  3. Most people are turned off by bad grammar. Also, if you're over 20, avoid using "netspeak," such as "u" for "you" or "r" for "are."
  4. If you send a couple of messages and he doesn't respond, stop trying to initiate conversation, especially if your messages are marked "read" by the messenger.
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Expert Q&A

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  • Question
    How can I use the internet to win a date?
    Maria Avgitidis
    Matchmaker & Dating Expert
    Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
    Matchmaker & Dating Expert
    Expert Answer
    You can use online dating as a tool to win a date. When you meet someone online, try to arrange for an offline date within a few days. First, you can comment on the profile of the person. If you get a response from them, it means that they also have an interest in you. You can go ahead and ask them to meet you in person.
  • Question
    How can I make a great first impression on someone I meet through the internet?
    Maria Avgitidis
    Matchmaker & Dating Expert
    Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
    Matchmaker & Dating Expert
    Expert Answer
    If you want to make the best first impression on someone whom you meet in person after meeting online, you should post a recent photo that looks like you. Secondly, it should look like you are on a date. If you are going on a date after work, get out of your work mentality and assume your date mentality. When you go on your first date, wear something that is comfortable and makes you look good. You can wear well-fit jeans or a good dress, and high heels or flat shoes.
  • Question
    How can I end the date if it goes badly?
    Maria Avgitidis
    Matchmaker & Dating Expert
    Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
    Matchmaker & Dating Expert
    Expert Answer
    If you do not want to have another date with a particular person, you can text them. You can say that it was nice meeting them. But unfortunately, you do not feel that there is long-term chemistry between you. Finally, you can wish them luck in their future search.
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