How to Ask Her Out on A Dating Site and Get a YES

Asking someone out can be stressful. The fear of rejection is always at the back of your mind and having unreciprocated feelings can sting. In online dating, from the relative safety afforded by your computer screen, you’d think it would be different. Easier.
 

It isn’t.
 

When the time comes to ask a woman you like out on a date, you feel the same tingle of anticipation. And the same apprehension. What if you’re misreading their intent, and they are not into you? What if they are interested, but you botch your message and you never hear from them again?
 

Fortunately for you, there are things you can do to get more positive responses to your invitations. A step by step process that translates to more dates and increases your chances for a relationship. Admittedly, it is not an infallible method, but will give good enough results for most guys.
 

Let’s have a look:

Forget about Cold Calling

Telemarketing is a tough job. Most people will either ignore you or not reply at all. Case in point: cold emails have a response rate of around 1%. The other 99% most likely felt bothered in their daily routine. Or not bothered enough to respond. And that is for qualified prospects that probably need the products or services offered.
 

Why would it be any different on a dating site? Sure, women are there to meet someone and, presumably, go on fun dates; but it doesn’t mean they’ll accept every offer that comes their way.
 

In fact, women are a great deal more selective than those telemarketing prospect. Asking to meet in your first message is almost guaranteed to fail.
 

Work up to it instead. There’s no rush; start with a few casual messages to get to know her. Take your time and don’t push a romantic date on someone who has no idea who you are.
 

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What You Should Talk About in Your First Few Messages

There’s a lot that can be said about opening messages on dating sites, but that’s a different topic. Just remember that when you are going to ask a woman out, you should first build rapport with her. Have a light conversation to start with.
 

You can spread your messages over a few days too. Ask some questions, nothing too deep, and share some information about you if she asks. Again, nothing too deep or personal. You’re trying to see if there’s a good feel between you two and potentially a good match to be made.
 

Why is this important?
 

Well, for one, it allows her to feel more comfortable chatting with you. Both you and her will be able to screen for any red flags too.
 

But just as importantly, you’ll get to know her, what she likes. If she’s a big music fan and allergic to seafood, she’ll be more excited at the thought of going to a live show than to dinner at the Red Lobster. Remember that when you ask her out.
 

It also allows some light flirting. A funny gif or a compliment will let her know how you feel about her. Again, don’t come on too strong. If she responds in kind, you’ll know where her head is at. The more she responds to your flirting, the more likely it is she’ll want to meet in person. 
 

Choose the Right Time to Make Your Move

So, you’ve made up your mind to invite her. You’ve been chatting long enough that the conversation feels natural and comfortable (but not so long that you’ve run out of things to say.)
 

It’s time to ask her out on a date.
 

Pick the right time to do it. Avoid doing it on a morning right before work and she has a busy day ahead of her. Likewise, if you know she is going to be out of town for a game, a friend’s wedding, or a family dinner, steer clear.
 

And of course, don’t ask her to hang out with you if you’re drunk or at a crazy hour of the night.
 

Choose a time you are both online. If she gave you her phone number and you can text her instead. Again, no cold calling.

What to Say When You Ask Her Out

Start with small talk. Simple messages like “How was your day/practice/the wedding?” or something else she mentioned will do the trick. But don’t wait too long to ask. You don’t want the conversation to be sidetracked (or worse, die down).
 

If you’ve taken the time to know her before, this is where it helps. Invite her to do something she’ll enjoy. No need to pressure her to answer or make a big deal out of it.
 

If you are less sure about her interest, you can leave things more open. Messages like “How would you like to meet up sometime?” or “We should meet up if you’re up for it,” also work well.

When She Replies…

If you’ve done your homework well and read the situation correctly, you should get a big “Yes, sure!” to your invitation.
 

In that case, congratulations. Confirm quickly when and where you’ll meet, and you both can look forward to meeting in person.
 

But be aware this is not always the case.
 

Sometimes she’ll give you a vague answer, or not really answer your question at all.
 

Does that mean she’s not interested?
 

Well, yes. Most likely.
 

See, women are very skilled at letting guys down easy. They’ve had more experience rejecting guys and are quite good with subtext. If they reject your advances, you’re not likely hear a clear “No thanks.”
 

If they are indeed interested, they will let you know. There is a big difference between “Oh no, I can’t hang out because my exams are coming up, but I’m all free after!” or “I’m not really into country music, but how about going to see this band instead?” and “Sorry, I have an early day on Thursday, so I prefer not going out on Wednesday.”

Accept Rejection Gracefully and Move On

Being rejected sucks. There’s no need to sugar-coat it.
 

But however subtly she turns you down, it is an opportunity for you to move on. There are many, many other women on dating sites who’d love a chance to meet you. There is no need to keep asking the same woman out repeatedly. Send her a quick message or two to end things on a high note but now the ball is in her court. She knows how you feel about meeting her.
 

And this is what trips up a lot of guys: sometimes the woman you asked out didn’t reject you outright but doesn’t seem to make much effort to meet you.
 

Instead of a long-winded explanation on how to deal with this specific case, let’s just quote the great Maya Angelou:
 

“Never make someone a priority when all you are is an option.”

And Finally

While these steps work well for most guys, they might not work for all guys. For every man that followed this template and got a date, there is one who didn’t, and is just as successful. Feel free to try it out and see if the responses you get improve. The key to your dating success will be to figure out what works best for you.
 

Good luck!