How to start a conversation with a guy

Olga Kachmar

Perhaps recently you have seen a boy whom you like so much, he is attractive and handsome. You meet him every morning at the bus stop and sometimes it seems to you that he throws a quick glance at you. That makes you really happy. I think that every girl has experienced such feelings at least once in a lifetime. But there is a problem, you don’t know how to start communication with that attractive guy. I will give you some recommendations which hopefully will help you to surmount your shyness and talk to the boy that seems so attractive to you.

Best Ways to Start a Conversation with a Man

Here’s what you can say:

  1. “You seem pretty stressed and tired these days. Something wearing you down?”

  2. “You haven’t seemed like yourself the last few weeks. Is anything up, maybe something I could help with?”

  3. “No matter what’s bothering you, I’m all ears. Don’t worry, I’m not here to judge you.”

  4. “I just want you to know that I have your back, whatever’s going on I’m open to helping out in whatever way I can.”

  5. “All this stuff is actually pretty common among men – it’s nothing to be ashamed of.”

  6. “I’m not an expert when it comes to this kind of thing, but there’s a site called HeadsUpGuys. It has lots of practical tips for dealing with stress and depression. Here I can show you…”

  7. “There’s a self check on this site called HeadsUpGuys, maybe try taking it and you can get a better sense of how you’re doing?”

  8. “I hate to see you down like this. You know if you’re not feeling right, there’s no shame in seeing a doctor and getting their advice.”

Get more tips on how you can provide initial and ongoing support for a guy you care about.

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1. Mention Their Interests

In a study by OkCupid, they show that the member would get a higher response rate for first messages that mention the specific interests of the person they’re talking to.


This may be personal interests (such as zombies and metal bands) but in marketing, it’s more likely to be a reference to something professional, such as:

  • A comment on a topic that they’ve mentioned recently: “I saw your post/tweet/article about pinball…”
  • A prediction they’ve made: “I see you predicted that arcade games are making a comeback…”
  • An opinion you share: “I totally agree with you that 80’s games are underrated…”
  • A compliment on something they created or accomplished: “You’ve got the high score on the pinball machine at SuperDawg. Congrats!”
  • A thank you for something useful they shared: “Thanks for sharing that article from Flipper Quarterly. I found that really useful…”

Mentioning an interest is your chance to show that you have something in common, and to do it in a positive way. 

2. Show That You Did Your Homework

How’d you find that interest? You read their profiles, you’ve read their content, you’ve researched their company. You’re listening and paying attention.

Everyone likes to be noticed.


If you’re starting a conversation with a high-value potential contact, like a prospect, job candidate, journalist, or influencer, dig deep into the research. Indicating that you’re deeply engaged makes a huge difference.

  • I read your book, and I agree that…

  • I’m subscribed to your podcast and I noticed that…

  • I’ve been reading your blog for the last few months and…

3. Be Humble and Self-Effacing

For guys on dating websites, this is life and death. The ladies can smell arrogance a mile away. Self-effacing language shows humility. But it also acknowledges the obvious: it’s awkward to contact someone out of the blue.

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Tip: A first message should be direct and concise. But if there’s a place for softened language, it’s in the one sentence that admits you’re coming at them out of nowhere.

4. Be Personal and Original

Another finding from the OkCupid study found that the most generic salutations get the worst results. “Hi” “Hey” and “Hello” were the most common openings, but also the least effective.


I’m not suggesting you start a message to a New York Times editor with “Yo!” The lesson here is this: don’t start by sounding like everyone else.

5. You can’t win if you don’t play …patiently

Any pickup artist will tell you that you’ve got to put yourself out there. Have the guts to reach out. No guts, no glory. But don’t rush it. It may be worth it to slowly put yourself on their radar in the days and weeks leading up to the first conversation.

Social media gives you all kinds of ways to do it. Here’s a sample of the 35 steps in the complete online networking guide…

  1. Follow them on Twitter or Google+ (which don’t require their approval)

  2. Share their content on Twitter or Google+ (and mention them)

  3. Comment on something they wrote (show that you thought about it)

  4. Share content on Facebook or LinkedIn (and mention them)

  5. Write something that refers to them (and quote, link, or credit them)

  6. Start a conversation (possibly mentioning what you wrote)

Once the conversation has begun, ask a follow up question. Open-ended questions work best. Avoid asking questions that can be answered with a single word.

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Once a good connection is make, you’re ready to politely ask for something. I find that an offer to collaborate is a great way to start.

Go for it, player! Ask her out!


Our friends at Bluewire Media created an excellent blogger outreach template. Enjoy!

Blogger Outreach Template from Bluewire Media

Bottom line

When attempting to talk to strangers you have to accept that the first few moments will be awkward sometimes, that some people will blank you – that’s just life. My experience tells me most people are very happy to have a chat and nobody will bite you! Your only challenge is breaking the ice and the conversation will flow from there.

Do you have any hot tips for talking to strangers? Or how to avoid strangers talking to you? Or how not to be strange? Please let us know in the comments!

Related: The Psychology of Networking: How Some Appear Natural While Others Stutter.

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