Get a conversation going first.
Asking someone out right away can be a little off-putting. Instead, try chatting with this guy back and forth for at least a couple of hours (or even a couple of days) before you make your move. There’s no rush to ask someone out, and talking to him online let’s you get to know them a little more before you ask them out. There’s no magic number of messages you should go for, but in general, 5 to 10 messages back and forth is the minimum.
Respond to something he posted.
This is a great way to start a conversation on social media. If you’re scrolling through Instagram and he posts a funny story, send him a message telling him that you just laughed out loud. If you’re on Twitter and he drops a hot selfie, DM him and tell him how good he looks. Social media posts are a great way to grab easy conversation starters without a ton of effort. For instance, after he posts a meme you might say, “LOL, where the heck did you find this??” In response to a cute selfie, you might say, “Wow, you’re a sight for sore eyes. You look great!”
Give him a few compliments.
This is a subtle way to let him know you’re interested. Keep your compliments relatively tame, and don’t say anything specific about his body or physique (since that can be a little weird to hear online). If this is your first time chatting, tell him he has a nice smile or that he takes great pictures. Try something like: “That picture you took of the mountain is so nice! I feel like I’m actually there.” “You have such a nice smile!”
Ask him questions about himself.
Show him that you’re interested in his life. Ask him a few open-ended questions to learn more about him and what he likes to do. You could chat about his hobbies, his friends, or even his pets if he has them. This is a great way to get to know each other a little more before you dive into asking him out. Try things like: “What do you get up to on the weekends?” “Who have you been hanging out with lately?” “Do you have any pets?”
Chat about your common interests.
There’s probably something you two have in common to talk about. If you don’t know him at all, take a quick look at his profile to see if anything lines up. This is a really good casual, non-creepy way to start chatting with a guy online. For instance, if you both like rock climbing, you might say, “Heading to the climb center this weekend?” If you checked out his profile and realized that you both love going hiking, you might say, “I just saw that pic you posted on your hike! That’s such a beautiful view, where is it?”
Tease him a little bit.
This is a subtle way to let him know that you’re interested. People usually only tease each other when they’re into them, so try poking fun at something he likes or something he did. Keep it super playful, and throw in an “lol” or a few emojis so he knows you’re not being serious. You could say something like: “Wow, you’ve never been to Disneyland? Idk if I can keep talking to you, lol.” “You got that project done early! Trying to get on the boss’s good side, huh? ????”
Flirt with him.
Flirting a little will prepare him for when you make the first move. As you two chat, keep giving him compliments and reminding him that you’re single to send the signal that you like him. Throw in some flirty emojis, like kissy faces or hearts, and see how he responds. If he flirts back, then you know you’re in the clear to make the first move! Try messages like: “Missed you at work today! ❤️” “Your hair looked really nice today ????”
Ask him if he has plans later to be subtle.
If you can’t quite tell if he likes you, try this. Ask him if he has plans this weekend or sometime after work, just to see what he says. If he doesn’t have plans, then you know he might be open to you asking him out. If he says he’s busy (and he doesn’t offer up an alternative), then it might be a sign that he’s just not into you. You could say something like: “Any big plans this weekend?” “Are you free at all next week?”
Be direct about asking him out.
It can be confusing if you don’t make specific plans. A lot of guys aren’t great at taking hints, so if you aren’t direct, he probably won’t get the message. When it comes to asking him out, make sure you tell him that it’s a date thing (not just a friend thing). That way, he’ll get the message that you like him! Plus, a lot of guys aren’t used to getting asked out, so you might have to make it really obvious.
Suggest a specific date activity.
Try doing something related to your common interests. When you’re crafting the perfect message to send this guy, try to think of a potential date idea instead of just asking him to hang out. This will show him that you’ve put a lot of thought into asking him out, and he’ll probably be more likely to say yes! Try something like: “Do you wanna go frisbee golfing with me on Saturday? We could grab drinks afterward.” “There’s a new coffee shop downtown I wanted to try. Want to meet me there after work on Tuesday?” Reader Poll: We asked 1037 wikiHow readers about which first date they’d like to go on the most, and only 8% said going rock climbing. [Take Poll] So, suggesting a more casual activity, like grabbing coffee or seeing a show, might be more fun for him.
Set a time and a date if he says yes.
If he’s open to going on a date, that’s great! Pat yourself on the back for a job well done, and then confirm the date and the time before signing off. If you’re on a dating app or social media, consider giving this guy your number before you stop messaging each other just in case he needs to get ahold of you. Then, you can wait patiently for your date to get to know this guy even more. You could say something like, “Awesome! So Friday at 2:00 then?”
Don’t take rejection personally.
Not everyone you ask out is going to say yes, and that’s okay. Putting yourself out there isn’t easy, and you still made the first move, which is super inspiring! If the guy you’re chatting with doesn’t want to go on a date with you, it’s probably best to move on. Remind yourself that it’s not your fault—you two probably just weren’t a good match. Rejection is rarely ever about you as a person. More often than not, someone saying no to a date is doing it because they’re dealing with their own problems.
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