I’m an active member in a lot of dating advice communities online, and one question I see men asking constantly is “I matched with this girl and we’ve been talking, how do I ask her out?”
Good news, it’s a lot easier than you might think. The most important thing to know is that women have a very different experience with online dating than us men do. Most women get a lot of likes. And when I say a lot, I mean that if they’re especially attractive, it can be hundreds of new likes every single day.
Sometimes thinking about this discrepancy can be discouraging for guys. Even the most attractive men tend to get only 40 or 50 likes per day, and for the average looking rest of us, it can be a lot lower. But don’t despair. The reason I bring up this difference is to give you some encouragement.
If a woman is responding to your messages on a dating app, she has chosen you over what is likely hundreds of other guys. Even more so if she’s putting effort into her messages and writing you a thoughtful response. But short messages don’t mean a lack of interest, it could be just the way she texts, it could be that she’s busy, the point is…
If she is replying, she is interested.
So, you’ve matched. You’ve messaged. She responded. Now what?
You exchange two or three messages each, then you ask her out.
Does that seem too soon? Here’s the truth. Most guys wait far too long before they ask a girl on a date.
Messaging is a terrible way to actually get to know someone. I’ve matched with girls and had incredible text chemistry, where we’d chat back and forth for hours, and then we met up and it was immediately clear we weren’t a good match. I’ve also had the opposite, where the texting was pretty dry, but once we got together in person the conversation flowed effortlessly and we had an amazing time.
You will learn so much more about whether you get along with someone during a 30 minute coffee date than you will with days or weeks of texting. These days, with most first dates being video calls anyway, you don’t even have to shell out a few bucks for coffee.
What do you think will happen if you ask her out and it’s “too soon”? Every time that’s happened to me, she’s replied with, “I’d rather keep messaging her for a while before we meet up.” Then I’ll say, “No problem” and we’ll keep chatting.
This is a good thing. Some guys I coach feel like this is bad because they’ve offended her, or they feel like they’re coming off as a creep.
I repeat, this is a good interaction. She set a boundary, and you’re showing her that you’re the kind of guy who respects her boundaries. She’s going to like you more, and be more interested in dating you after an interaction like that. I guarantee every woman you have ever met has multiple experiences of guys who push past her boundaries, don’t take no for an answer, and do not listen. She doesn’t want that.
By respecting her boundaries you are building trust, and trust is a core part of a healthy, happy relationship.
And there’s a pretty good chance if you ask her out after two or three messages she’ll just say yes.
Okay, so you’re ready to make a move in a timely fashion and ask her out. How do you do it?
Most of my conversations with girls on dating apps go like this:
We match, and I send her a question about something in her profile that I’m interested in. Or maybe one of her pictures is really interesting, so I ask about that. I always open with a question and it should be one that is both easy and fun to answer. And positive. Don’t ask a downer.
I like talking about goals and aspirations, so I’ll usually find something about her job, or her plans for the future and ask about that. “What inspired you to go back to grad school?” or “You mentioned your current job is the most fulfilling one you’ve ever had, what makes it a great match for you?”
If you’re really stumped you can always use ol’ reliable. Find a picture of her traveling or in an interesting location (most women have one) and ask her, “Hey that picture of you at the _ is really cool, where is that?”
Specific questions are always better, so you should try to find something you’re interested in talking about.
If she responds, congratulations! She likes you. She may ask a question in return, either a new one or “What about you?” Even if she doesn’t, feel free to answer your own question in return. Here’s an example of what I mean.
Let’s say this girl’s profile says, among other things, that she loves Taylor Swift and she ordered a ukulele to play because of the covid pandemic.
You: “Hey, I see you’re learning to play the ukulele in quarantine, how’s that going? Mostly playing Taylor Swift songs?”
Her: “Haha, of course! Taylor Swift makes any day better.”
A lot of guys stumble here, but there are two ways you can pretty much always respond. First, you can ask a follow-up question. In this case, the only thing to respond to is Taylor Swift, so I would say something like…
You: “I’m a Taylor Swift novice, don’t judge me. If I want to see what the hype is all about, what should I listen to first?”
Another good approach is to assume there’s an implied “What about you?” at the end of a response like that. In this case, you’ll have to take a step back and make it more general, what have you been doing to pass the time in quarantine? Any new hobbies or interests? For example:
You: “I’m sure you’ll be performing on stage in no time! I’ve been getting into breadmaking like everybody else, it’s going… okay, haha. How long have you been practicing ukulele?”
Notice at the end, I keep the conversation on the same topic. Jumping around from topic to topic can be jarring, and you really want to stay focused.
Either way, you’ve asked her another question, she’ll respond, and then you might send one more message, but either way you can then deploy my favorite line for asking her out.
“Would you like to keep talking over a cup of coffee?”
In these pandemic times, I’ll usually say, “Would you like to keep talking on a virtual date?”
It’s that easy.
If she says yes, which she probably will, I like to suggest two times, usually a weekday and a weekend. This speeds up the scheduling process and you don’t have to play as much text message tennis.
Her: “Sure! That sounds good. :)”
You: “Great! I’m free on Wednesday evening or Saturday afternoon, let me if either of those is good for you.”
Just a quick note, if she can’t make it or says she’ll get back to you about her schedule, give her the benefit of the doubt. This is a great opportunity to find out if she’s a good communicator. If she says she’ll text you after she gets her work schedule, and then she does it, that’s a great sign. If she leaves you hanging, that means you should move on and find someone who’ll put in some effort. Either way, you’ve learned something important.
Most likely she’ll tell you one of those days is good, then you can lock in a particular time and place.
Just don’t forget to text either the day before or the morning of the date to confirm. It can be simple, I usually say, “I hope you’re having a good week, I’m looking forward to seeing you at 2 tomorrow!”
In conclusion, ask her out after two or three messages. Suggest continuing your conversation on a date, and give her a choice of two days. Then lock in a time, suggest a place, and you’ve got yourself a date!
If you really want to get the confidence to message women and ask them out, consider booking a consultation call with me. We can definitely get you more dates, virtual or otherwise.