How to Turn Online Dating Conversations Into Real Dates (Step-by-Step Scripts)

I think this is the biggest trap that online daters fall in. So many profiles to swipe on. So many “hey” messages sent. But nothing comes out of it. Zero actual dates get on the calendar.

It’s all aimless small talk and a one-way ticket to online dating burnout.

How do you up your conversion rate and make all that time spent on the dating apps worth it? I’ve got some suggestions based on my experience reviewing dating apps for over 10 years and using them in my personal life for most of my 20s.

I know the common mistakes that lead chats to fizzle. And I know what strategies helped me go on about one date a week until I stopped dating forever. I met my husband on Hinge, so I’m not just talking… I’ve also walked the walk, as the saying goes.

Let’s start at the beginning. You have a match. Now what?

Step 1: Have an Engaging and Personalized Opener

Don’t just say “Hi.” Ask something deeper than “How are you?” Such generic opening messages are instantly forgettable and easy to ignore or overlook.

If you’re a straight single man, you’re facing particularly steeper competition because of the social expectation of men messaging first. A woman might receive 5-10 messages in a day. 

If your opener just says “Hi there, how are you?” while someone else asks her about her trip to Spain, who do you think she’s going to invest time in answering? 

Take the time to read a profile and study the photos so you can mention at least one specific in your message. It’s a sign of respect and interest. It shows you’re not just here to copy/paste the same line to everybody.

That last one is good to use if the profile is giving few details, and you just want to know where they stand and if it could be a compatible match. Basically, the only thing you know you have in common is you’re on the same app, so it’s best to start there.

And if you want to know the line that got me to swipe yes on my husband, it was a compliment on my photo dressed as Catwoman in a movie theater. I didn’t have a mask, so I had scribbled mascara across my face. “You have a smidge of cute on your face,” he wrote. “What movie were you seeing?”

That question started a conversation about Marvel and DC movies, and a little over a week later we went on our last first date. That brings me to my next tip.

Step 2: Ask Questions

I remember vividly one of my friends complaining that no one ever answered his messages. He was a 24-year-old med student. He was polite, if a bit goofy, and took good care of himself. He had “Golden Retriever energy” long before that was a thing.

I was perplexed about why girls were snubbing him. Then he handed me his phone, I read his messages, and I understood.

“You’re not asking any follow-up questions,” I told him.

The conversations weren’t ending — he was ending them. He’d compliment her dog, she’d ask if he had any dogs, he would talk about his dog growing up. And then he wouldn’t ask her anything! So many periods. All the question marks were coming from the women.

Online conversations take a lot of effort and time, and if you’re making the other person do all the work of keeping the conversation going, they’re going to get real tired of that real quick.

Don’t be that guy. Be better than that guy (sorry, Danny!).

Ideally, you’re avoiding simple yes/no questions and getting into specific characteristics and habits that’ll give you insight into who they are (and if you want to date them).

This doesn’t have to be soul-searching thought-provoking stuff. A simple “how about you?” would work. 

The whole point is simply to show that you want to keep chatting and aren’t just a megalomaniac only interested in long diatribes about yourself and your favorite childhood puppy (no shade, Danny, you figured it out eventually).

Step 3: Plan a Specific Date

Avoid vague invites like: “Want to hang out sometime?” That’s not a plan that anybody feels excited about.

When I was dating, I had a theory that anytime someone said, “Let’s try for next week,” or “I’m free week after next,” that coffee date was not actually going to happen. You’re losing momentum by putting the date off.

Your approach should be confident and specific about what type of date you’re wanting. And it should be soon enough that they won’t be distracted and forget about you.

These invites all reference specific ideas and days. And they all end in a question so the planning is collaborative.

You’re not dictating a plan. You’re seeking input for what the plan should be. Showing flexibility and courtesy in this stage can go a long way to cement the new connection.

Be friendly but casual, and make sure the person knows they can say “no” without triggering any angst or hissy fits. If they make an excuse, accept it with grace. 

Say something like “Well, maybe next time” or “I get it. I don’t mean to be forward, but I am interested in meeting in person when you’re ready.”

Specific Scenarios: What If They Stop Answering?

First of all, did you ask a question in your last message? If no, then go ask a polite question, ideally something related to the conversation. 

If you can, reference a topic from earlier in your conversation. Even if it’s a comment about the weather, the point is simply to get back on the person’s radar and see if a new question can restart things.

Now, if your last message did have a question, this may sting. You’ve been ghosted. If you can’t let it go, send ONE follow-up. “Hey, how’s your day going?” Or some other casual question with a friendly tone.

No answer still? Go back to the swiping scene and match with another profile. Hopefully, the next person will show better courtesy!

What If They’re Lukewarm & Giving Mixed Signals?

The more cagey an online match is being, the more direct and clear you need to be. Don’t play games with game players. Everyone just ends up wasting time.

These confirmation messages shouldn’t be blaming or accusing. It’s a check-in to essentially say: “I’m here. Where are you?”

If you don’t get a clear answer and know where things stand, that means you’re being strung along and the connection just isn’t strong enough to warrant continuing chasing the person down.

How Do I Make Things Move Faster?

Look, if the back-and-forth online messaging isn’t your jam, that’s fine as long as you know that about yourself.

I personally enjoyed the pen pal phase. But sometimes that meant I engaged in chats longer than I should’ve. Getting to an in-person date more quickly certainly saves time. But it won’t happen on its own. You’ll need to steel your courage and make that move.

Not everyone likes texting. There are mixed signals and long unexplained pauses. And emojis.

You don’t have to text for a month before going on a date. Give it a couple of days, and then make your ask. If you’re a straight man, you might run into some no’s simply because you’re moving so quickly, and you have to respect those boundaries. 

But some people will be open to it. The only way you’ll know is to ask.

What If They Say No to Going on a Date?

Be curious about the why. Are they just busy and another day would work? Or are they not feeling the same level of interest and attraction? 

The first one is easily solved. The second one is probably not going to change (it’s possible, but extremely difficult to turn a no into a yes).

Only you can determine if it’s worth sticking it out, or if it’s better to move on.

Keep Going & Stay Positive

Look, I get that the swipe game can get demoralizing. Really, I know. I’ve gotten excited about matches only to see them fade to nothing for no discernible reason. 

Some conversations just never become in-person dates. Maybe she met someone she liked better. Maybe he got distracted by a butterfly. It doesn’t matter why. It matters what you do next (hint: it’s not sulk or cyberstalk).

One of the most important skills you can have as an online dater is resilience. Just because that match didn’t work, that doesn’t mean the system is broken and your only choice is to give up. Keep your chin up and find another match.

If it doesn’t seem like your strategy is working, then adjust. I tried several different approaches until I found what worked for me. At one point, I was juggling four different dating apps. By the time I met my husband, I’d become a Hinge specialist.

No online dating strategy will have a 100% success rate because trial-and-error is baked into the process. So don’t let the failure get you down. Staying positive and persistent will keep you on a good path so you’re more likely to land a date next time.