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How to Keep a Conversation Going on a Dating App With a Woman You Want to Meet

How to Keep a Conversation Going on a Dating App With a Woman You Want to Meet

Whoever thought that a pandemic could be a solid wingman?

Since coronavirus touched down in the US, the length of Tinder conversations has increased between 10-30%. It makes sense doesn’t it? Nowadays because of stay at home orders Americans are spending more time alone in their homes. It’s this free time compounded by their newfound loneliness that’s leading Americans to chat even longer on dating apps like Tinder.

However, the protracted conversational bump provided by the pandemic is temporary (if it’s even around when you’re reading this). You can’t rely on highly contagious upper respiratory viruses to bolster your online dating game forever can you?



A more sustainable option to upping your online dating skills is learning how to keep a conversation going on a dating app.

In this article, I’ll train you how to carry on a conversation that doesn’t fizzle out and ultimately leads to an exchange of numbers or a first date.

All the information I’ll provide you with today comes from a session I recently had with a client that was struggling to converse with women through dating apps.

How to Keep a Conversation Going on a Dating App That Leads to a Real Life Date

Stick to Topics Related to Hobbies, Favorites, Family, or Pets

talk about pets on a dating app

Your goal in talking with women online is to have a conversation long enough to determine whether or not you want to go out with her and vice versa. The best way to prolong a conversation is to discuss her interests.

When in doubt, shape the conversation so that it revolves around her interests. If someone took an interest in your interests you’d be inclined to chat it up all night wouldn’t you?

When discussing things that pique her interest keep the conversation emotional rather than logical. Dating -especially the early stages- are about gut emotions and sensations. She isn’t asking herself after the first message if you’re going to make a good father or not.

Invite her into the conversation by poking at her heartstrings. Ask her about the dog in her photos that she adopted by a kill-shelter or her love for snorkeling in the Great Barrier Reef. Always stick to the topics that will elicit and emotional reaction and keep her talking. Her hobbies, favorites, family, and pets are all wells of emotional material that you can tap.

An example of an opening message that’s sure to receive a response is any message that asks a question of one of the aforementioned topics. If she can be seen playing water polo or dancing, ask her why she picked up water polo or what her favorite type of dance is. Being that you’re offering to talk about a topic she’s interested in and have shown that you actually read her profile, she’s likely to respond.

Keep this spark of a conversation going by continuing to inquire about her interests while gently steering the conversation towards a TDL.



Don’t Skip Around on the Surface, Create Depth by Going Deep with the Topic

how to keep a conversation going on a dating app - go deep

The worst thing you could do is skip around to various topics without ever going deep.

Sure you could pepper her with questions about all her hobbies, her favorite shows, foods, etc. But that’s all surface-level conversation. To crack her open you’ll need to ask penetrating questions. Let’s give you an example of what going deep looks like.

Let’s say she’s a chess fan. You know this because she’s both written about it in her profile and she’s playing chess in one of her photos. Start off the conversation by perhaps jokingly asking her if she could best Magnus Carlsen in a game of chess. Being that she’s a chess-head she’s bound to appreciate that you know how Magnus Carlsen is and respond.

Now it’s time to plunge into the deep end of the conversation by asking her why she started playing chess or if he family got her into the game. She might respond by telling you that she used to play with her Mom on long car trips and that she’s been playing even since her first ski-trip to Colorado Springs. It’s at this point that you can dive even deeper or connect this topic to a related one. You could ask her where she used to travel when she was a kid and add that you always used to sail up and down the Long Island sound with your parents when you were younger.

If you two share an odd interest, vibe on that until you score a phone number or ask her out. If you feel as though the topic may be running its course switch to a different one that’s already been broached.

Throughout the course of the conversation keep showing interest in her. Don’t comment on how hot she is or ask her why she’s single, keep trying to figure out who she is through these probing questions.

Learning more about her by asking about her interests doesn’t mean interrogation. Bring levity and humor into the conversation and don’t forget to tell her about yourself.

Augment The Emotional Response Elicited By Your Questions

keeping a conversation going on a dating app

With the myriad of women you may be chatting with online, it can be tempting to put minimal effort into constructing a message. It’s tempting to sloppily converse with her before praying she gives you her number when asked. You can treat online dating this way, but you’ll fail.

Instead, treat each message as though it were a line of poetry.

Each word must be significant. Ask yourself why you’re asking her this question, why pose it in such a way, and what the coveted response is.



Look, for as many women as you’re courting with online she’s chatting it up with five times as many men – guaranteed. The competition is high on these apps. So high that a study found that men only have a 4% chance of receiving a response on dating apps. On average a single man using Bumble will need to send 18 messages to have just a 50% of receiving just one response.

Look women aren’t going to settle for mediocrity when they’re being pursued so vigorously online. They can sit back, sip a margarita and choose who they want to give their attention to.

Stand out by investing time into the conversation process.

When trying to hook a female user, give her something to bite on. “Hey,” “hey there cutie,” and “hola” will not work. Period. Engage her by asking her a question about something she’s interested in as we’ve already discussed.

After you’ve received an initial response it’s time to ask probing questions. Learn how she is by asking emotionally charged questions. Discuss topics that she enjoys. Once you have her talking learn more about her by asking penetrating questions pertaining to her interests. Breaking down barriers is the best way to build a connection.

So many of her interactions via online dating are superficial. She’ll chat about there favorite Netflix shows but never feel as though the person on the other side of the screen really cares to know her. Make your worth known by transcending the tradition Tinder conversation and eliciting emotional responses.

Ask Questions You Want The Answer To

asking questions on dating apps

This conversation isn’t all about her.

If you have zero interest in polo, don’t inquire about it. You probably don’t care about her job, the weather, how long she’s lived in the city, etc.

Your goal with these conversations is to learn enough about the woman to determine whether or not she’s worth your time. You won’t learn that if you keep asking her about her favorite Coldplay song.

If you’re MegaDating effectively, you too will have women knocking at your door. Don’t waste your time or her by asking questions you don’t even want to hear the answer to. Get to know her enough to figure out if she’s worth meeting in person. You do this by opening her up with emotional questions. Stay away from logical topics like work and focus on what makes her feel alive.



As much as possible ditch the surface level questions in favor of ones that peel back layers of her personality. The last thing either of you want is another vapid online dating conversation.

Share A Secret

sharing a secret

She’s much more likely to be vulnerable if you open up first.

A favorite opening line of mine is, “tell me a secret” or “tell me something cool about you.” When men message women these lines, they often will receive the response of, “you first.” Show her that you’re not scared about opening up and are willing to be vulnerable with a complete stranger.

I guarantee this isn’t a cliche opening line. This being the case she’ll be intrigued by your secrete and once shared will likely reciprocate.

Keep whatever secret you share light enough that you don’t scare her away. Always stay away from depressing topics. Instead, tell her something silly you did when you were younger or a weird habit you do that not many people know about. After secrets have been shared, if it feels right probe her a bit about her secret. If this option isn’t on the table, pull back and ask her another probing question about herself. Considering she already has her foot in the door emotionally, it’s likely she’ll continue to open up to you.

Transitioning Into The Real World

real life date

What is considered a successful online dating conversation?

Is it one where she opens up to you by telling you all about her hopes and dreams? Or is success defined by the number of exchanges?

Realize that chatting it up via a dating app isn’t considered dating. In fact, even the term, “dating app” is a bit of a misnomer.

Biological anthropologist, author of The Anatomy of Love and Match.com’s Chief Scientific Advisor, Helen Fisher says that dating apps should be viewed as introduction apps, rather than dating apps. She urges users to get out of the app as quickly as possible so that they can begin the courting phase.

Ya see, dating apps offer the opportunity to speed date women, just in an even more superficial way. There is only so much that users can emotionally and socially gain from even an in-depth discussion via the apps.



To me, a successful dating app interaction checks off a few boxes.

One box is that you find someone worth dating. It’s great if the woman you’re talking to is into you, but if you don’t reciprocate, the conversation was all for not.

The second box is that you scored a phone number or date. If this doesn’t happen the match you’ve been chatting with is nothing more than a virtual pen pal. So just how do you make this transition?

Naturally, you’ll want to steer the conversation towards a TDL otherwise known as time, date, location.

As we’ve discussed begin the conversation by touching one of these categories: hobbies, favorites, family, or pets. After chatting for a while, ask her on a date that relates to what you’ve just been discussing. If you’ve been talking about your pets, why not ask to go on a walk around a park or to the dog park with your pooches. If you’ve been discussing the fact that you two are both runners, bikers, or hikers, ask her out on a date that relates to her hobbies.

When asking her out, don’t ask her on a date that takes place during the amorphous future. Give her a concrete date request that she can either accept her reject. Ask her to go hiking at Mount Sutro, this Sunday, at 11 a.m. This way she’ll have to offer you a yes or no answer.

Hire A Coach

Even if you’ve taken all the aforementioned tips on how to keep a conversation going on a dating app you still aren’t guaranteed success. Engaging in successful online dating conversations that convert into real dates isn’t an easy skill. To understand the ins and out of online dating you’ll need to sit down with a professional wingwoman. 

Book a new client 1-on-1 Zoom session with me today and I’ll walk you through what steps you need to take to have a successful dating app conversation. We’ll also discuss your current dating obstacles, create an action plan, and see if my three month coaching program is right for you.

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