How to have a great first date with women you meet online

Getting a first date can be hard. Getting that second date can be harder.

I’ve had a lot of first dates with women I met online that have not led to second dates. I’ve had women tell me that they didn’t feel a romantic connection. I’ve had women tell me that they’d rather be friends. I’ve had women agree to go on a second date and then later cancel on our plans.

And, occasionally, I’ve had women just stop texting me altogether.

Ghosts…they’re no fun!

When you meeting her from the internet for the first time, how do you have a great first date with her so that she’ll want to have a second date with you?

Do your research beforehand

Back when I started using OKCupid for the very first time, I was worried about getting no dates at all. So I sent out messages almost all the women that I saw there even if their personalities were drastically different than mine. I’d message her even if OKC said we were only a 20% match, or if she said that she hated dogs, or if she believed that the Empire did nothing wrong in Star Wars (I mean, seriously? Who thinks that?!)

None of these dates went anywhere.

Take some time and read her online dating profile beforehand to get a sense of what kind of person she is. Try to understand what her personality is like before you reach out to her. If she doesn’t sound like someone you can get along with then it might not be worth messaging her. On the other hand, if she sounds like a cool person then go right ahead!

Also, don’t lie in your dating profile. If she says that she prefers taller men and you don’t meet her requirements, you’re not going to change her mind. Don’t waste your time talking to her. Just move on.

Pick the right venue

When I first started online dating, I always asked the women I matched with out to dinner…I’d always assumed that it’s what you were supposed to do. One time I went on a date at a restaurant downtown. It was a fairly nice restaurant and we tried to make conversation, but it was mostly stilted and we ended up having most of the date in awkward silence. After we finished, she told me “This was ok, but I think Dave & Buster’s would have been more fun.”

“Huh,” I responded. “That actually would have been more fun!”

Getting dinner and/or a movie together is a common date activity that you see on TV, but it’s not something that I recommend doing for a first date. It’s too hard to interact with each other or have fun together.

What are some good ideas for a first date?

I’ve had good results with local coffee shops or cafes—not Starbucks, but places that provide a more intimate atmosphere. Another date idea I enjoy is meeting her to play some sort of gaming activity, such as mini-golf, bowling, or even the arcade! It’s easy to break the ice when you’re interacting with each other and having fun.

Pre-date communication

In the days leading up to the date, I like to text her informally beforehand. You don’t have to—it’s certainly not a requirement—but in my experience it helps break the ice so that the first meeting more resembles two acquaintances coming together than two strangers.

Text her with about the same frequency that she texts you. If she only texts you once a day then don’t send her a text once every hour. Finally, make sure that you’re being authentic when you text her. It’s easy to fake a persona through text, but if she meets up with you and you’re a totally different person then the two of you are going nowhere fast.

Talking to her during the date

Before going on a first date, research her dating profile to find things to talk to her about. If you’re using OKC, go through some of the questions she answered about herself and pick out a few interesting ones to talk to her about. One woman that I went out with said that she loves debating ideas. So, I came up with a few lighthearted questions to debate her about such as “What would happen if you replaced every molecule of water in the Earth’s atmosphere with a full-grown gorilla?” or “Muggles vs wizards? Who would win?” and then I always tried to argue the opposite of what she thought. She appreciated this and we had a lot of fun.

As you talk to her during the date, try to find things that she would enjoy telling you about herself. A great way to do this is by asking open-ended or “why?” questions. When she tells you something about herself, listen to what she has to say. Show genuine interest in what she tells you and ask some follow-up questions based on what she just told you or relate it to yourself.

If she is interested in you, then she would probably like to learn more about you too. Just like how we looked for things that she would love to tell you about herself, she will be looking to talk to you about the things that get you excited.

One woman that I met up with didn’t want to go on a second date with me, and she later told me it was because I was boring to talk to. When she asked me questions, I would give one answers and then shut up. For example, she would ask me “What do you like to do?” and I would just say “reading.” She then asked me “What’s your favorite book?” and I just said “Harry Potter”.

Even my dog thought I was boring!

Later, I realized that it wasn’t important what my favorite book is or what my hobbies were, but why. A more interesting response would have been for me to say “I really like Harry Potter because when you’re young, you want to believe that magic is real, and Harry Potter lets you experience that.”

Does she ask you open-ended questions about yourself? This basically means, “I want to learn more about you.” Tell her about some of the things that make you an interesting person. Do you have an awesome job? An adventurous story? Read something unusual recently? Tell her about it! Try to find something that the two of you are passionate about or have in common.

Be your best authentic self while talking to her, and try to match her personality while being true to yourself. If she teases you during the date then tease her back. If she’s more playful then feel free to act more playful as well, but do it to the extent that you are true to your own personality.

Finally, keep it lighthearted as you talk to her. Don’t require the date to go in a specific direction. Just relax and have fun.

After the date

If you liked her, don’t wait three days to call her. I’ve tried doing that in the past and it never worked for me. Instead, what I like to do is text her later that night and say “Hey [name], I had a really great time tonight doing [activity] and I’d really like to get to know you better :)”

Getting that second date

Getting a first date can be hard. Getting that second date can be harder.

As much as I want to give you a list of tactics that will guarantee a second date…it just doesn’t exist. Sometimes you can do everything right and still not tick all of her boxes or get her to feel that romantic connection. It’s happened to me a lot.

That being said, there are a few things you can do to maximize your chances.

Reach out to women that you thing may be a good match based on her profile and pick a good place to go for the first date. As you talk to her, show genuine interest and be interesting yourself. Keep it lighthearted and fun. And for goodness’ sake, if you liked her then don’t wait three days to call her again!

Above all, be your best authentic self when interacting with women. That’s the best way to be attractive.

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