Asking a woman out isn’t easy—especially online. It’s a moment where you have to be vulnerable, knowing the answer could be “no,” and so many men (understandably) fear rejection. Even digitally, the chance of being turned down exists.

As a digital dating coach, I find that many men either skip the chit chat with a match and ask her out right away to get it over with, or continue the conversation for too long because they’re not sure how to find the moment online. Either way, you risk losing her interest.

Here’s the deal: Asking her out online isn’t just about knowing what question to ask or when to ask it. It’s about developing a digital dynamic so she says “yes” when you ask her out. Follow these steps to connect with her in a way that makes asking her out simple and her answer (yes!) a no-brainer.

Laurie Davis Edwards is a digital dating expert and founder of eflirt.

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Online dating profile

Skip “hi.”

Most messages women get say “hey” or “hi” … and that’s it. Studies show you should skip a greeting altogether in your initial message, and that’s what works best for my clients as well. Instead, jump into conversation with context. On sites, three to four sentences works best for my clients and on apps, one to two sentences is best. Either way, make sure you end with a question so it’s easy for her to write back.

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Wait until you’ve built a mini rapport

Once someone (finally) responds, most men want to skip right to asking her out. The whole point of dating online is get offline, but it’s unlikely she’ll say yes if you don’t build a rapport first. Women want to know why they should meet up with you, not just that you’re interested. Focus on connecting so she’s less likely to ghost in your message string. Knowing each other better will mean a less awkward date, too. Once you’ve exchanged about six messages total on a dating site or around twenty on an app, the rapport should be strong enough to get a “yes” to date night.


Show you’re into her

My female clients always hesitate to go out with guys who don’t ask many questions. They wonder, “Is he too self absorbed?” Asking her questions will show genuine interest on your part.  Like on a date, you need to listen as much as you talk—and to digitally listen, you need to ask. It can be as simple as finding out the story behind one of her photos.

Qualify yourself

To show a woman why you’d be a good match for her, read her profile. It’s that simple. Creating conversation around similar interests will qualify you in her eyes, and make it more likely that she’ll say yes when you ask her out.

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Make her laugh

Messaging with a match develops a dynamic, and making her laugh will speed that up. Laughing is often associated with flirting, and a study on laughter and relationships found the more a man can make a woman laugh, the better the chance of a relationship. But remember: this person hasn’t met you yet, so it’s unlikely she’ll totally get your humor until then, and digitally, humor can come across differently. Being funny is great, but there’s no need to force it. Stay away from self-depreciating humor and sarcasm since they can come off negatively on screen. 

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Compliment her personality

Compliments only work online if they have nothing to do with her appearance. Since you haven’t really seen her yet, telling her how beautiful she is won’t seem genuine. Women still appreciate compliments though! Make her feel good by letting her know what you dig about her personality instead. For example, if she mentions she volunteers, let her know that you think it’s cool that she gives back. The best compliments to give are over topics you have in common and save the physical compliments for your date.

Learn what she likes

When you ask the right questions, you learn more about her. And then when you do ask her out, you can do it with relevance. For example, perhaps you both like live music. Asking her out to a spot with a great band will show special thought and attention. 

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Ask her out on a weeknight

Weekends are precious—yours and your date’s included. This is the first time you’re meeting so she shouldn’t take priority in your world yet. 

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Suggest drinks.

Asking her out for drinks is still the best date because it creates the right ambiance for creating chemistry—dim lights, close proximity, perhaps a candle or two. It can be as simple as something like, “I’ve been having so much fun chatting. Want to take it offline over a drink this week?”  If you’re on a cleanse or don’t drink you can still meet at a bar—just let her know before you meet so it’s not awkward. Chemistry is what’s been missing in your online interactions, so you want to make sure you put both of you in the best position for sparks to fly.

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