How To Start A Conversation That Ends With A Guy Asking You Out
How to be the woman no guy can resist — even online.
pics five | Shutterstock Starting a conversation and keeping it going is a big part of the online dating process. You can spend forever crafting the perfect online dating profile, but it won’t matter if you don’t know how to break the ice and get a winning conversation started!
While it might be tempting to send a simple "hello," those mundane conversations won't lead to a date.
16 tips for starting a convo online that leads to a guy asking you out
1. Examine their profile for clues
Successful online daters use the profile and photo gallery to give you "hooks" to help you engage.
Their profile may list a particular interest or achievement. Maybe they work in an interesting field or have a unique dream. Mentioning this in the form of a playful compliment or question can break the ice and show that you pay attention.
For example, if you’re looking through their profile and see exotic travel photos or them running an Ironman competition, then you know these are things they're passionate about — use them.
2. Ask them what they think
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A simple, non-threatening request for an opinion is a great way to kick things off. People love to show off how smart they are and can’t resist the opportunity to give their opinions.
Make a statement and then ask for feedback. For example, say, "I just got a new profile photo. I think it’s pretty good, what do you think of it?"
3. Ask for a small favor
Based on the concept of cognitive dissonance, research shows that if you ask for a small favor and someone grants it, they are more inclined to like and engage with you. This is because they convince themselves that they must like the person who they helped, otherwise, they wouldn't have done them the favor.
In the real world, this might be like asking someone, "Do you know what time it is?"
In online dating, it's something like, "Can I ask you a favor? I just worked on my profile. Can you tell me what you think?”
4. Stir pleasant memories
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People usually have fond memories of the physical place they grew up. If the person mentions where they grew up on their profile, consider asking them about it.
For example, you might say, "What was it like growing up in your hometown?" Or, if you've been there, you can say, "I just visited your hometown. What was it like growing up there?"
It’s important to stick to asking questions about the place, not about their family or schooling as these can be negative triggers.
5. Share your experiences
If you're both using the same online dating site, you probably live in the same area. Ask them about their favorite local recreation activity or any other generic — but geographically local — endeavors.
A shared experience can help you get a conversation off to a good start.
6. Introduce a 'negative'
For example, "So, what’s the worst date you’ve ever been on?" is a bit bold as an opener. But, this reminds the person you’re messaging that you're in the same boat when it comes to online dating.
By asking this question, you can avoid making the same mistakes as their past dates. You’ll learn what food they hate or just where they don’t want to be taken.
It also gives you an insight into their personality. Their reaction to the question can help weed out people whose expectations are too high or who just seem rude or cruel to others.
7. Reference pop culture
Show you’re in on the pop culture trends by throwing an unexpected online conversation starter someone’s way. Ask them what they think a celebrity, band, or reality show star is up to now.
People hear the same three lines every day online. Go beyond the mind-numbing, "Hey, what’s up?"
8. Ask, 'What's the last thing... ?'
This allows you to fill in the blank with pretty much anything you want. Ask them about the last concert they saw, the last time they traveled, or the last movie they went to see.
This is an easy question that also gives insight into the kinds of things they like.
9. Share vulnerabilities
We all fall on our faces from time to time. Just brush it off and keep moving forward.
You’re looking for someone who is OK with laughing at their mistakes. Asking about embarrassing moments allows you to gauge their comfort level with you, depending on how much they choose to reveal.
10. Ask about pets
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If you have or had a pet, start with a short story about something funny or cute your pet does or did. Then, if they also have a pet, ask them if they have any good pet stories.
11. Dream big
Play into the sense of possibility and excitement that comes from a new relationship by asking things like, "If money were no object and you could quit your job tomorrow, where would you go and what would you do?"
Everyone likes to have a fantasy and asking someone about theirs will help you get to know what they value most in life.
12. Play Desert Island
Send a message asking them to tell you which book, movie, and TV show they would take with them if they were going to be stranded on a desert island for the rest of their lives.
You could also ask which objects they would take with them, revealing a lot about them and their priorities.
13. Ask for their advice
People love feeling like their opinion matters, so show the person you’re chatting with you care about theirs!
For example, if someone’s profile has a lot of travel pictures, ask, "Hey, I noticed you seem to travel a lot. Any suggestions for my four-day weekend?"
This allows them to talk about the things they’re passionate about, which helps you learn about a person, not a profile.
14. Be funny, if you can
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Most people enjoy having a laugh. Start with a knock-knock joke or tell them a funny story.
Pick something from one of their photos and lightly make fun of them for it. Is that really his dog or is he borrowing it in an attempt to attract women? Was it necessary for him to have his shirt off at that party?
This creates intimacy and also allows you to see if they can take a joke.
15. Get to the point
If you’re using an app like Tinder, you already know the other person finds you attractive, since they had to match with you. Consider asking "Drinks soon?" or "Free this week?"
16. Talk about the future
You can involve some humor, as well. A simple question like, "So, two kids or three?" can get a laugh and show you’re serious about meeting someone.
Many people use dating apps and websites for hookups — according to the Pew Research Center, just 44% of users are looking to meet a long-term partner.
For people who are serious about finding a partner, it can be annoying to only get messages from people looking for a fling. Demonstrating you’re looking for something a little more serious (even as part of a joke) can help you stand out from all the other people sending messages like, "You’re hot."
Bonus Tip: Proofread your messages before sending them. Make sure you’ve spelled the person’s name correctly. Look for grammatical errors or spelling mistakes.
You don’t need to be Shakespeare, but you also need to make a good first impression, especially if you want the conversation to end in a date.
Claire Bahn is a dating and personal branding expert and CEO / Co-Founder of Stratus Branding and Online Profile Pros.