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How to Keep a Woman Interested in Online Conversation

JC is a psychology graduate with a passion in writing on topics about life, relationships, and more.

Article Overview

  • Online Dating: The Good, the Bad, and the Ugly
  • The Reality of Online Dating for Some Men
  • 7 Tips to Keep Women Interested in Your Conversation and With You
  • Final Thoughts

Online Dating: The Good, the Bad, and the Ugly

Online dating paved the way for a relatively easier dating experience compared to the previous centuries.

Online dating is the term used to describe the act of engaging in dating activities with the use of the internet and virtual space with the goal to seek for a romantic partner. It ranges from the use of online messaging sites, dating websites, and dating applications, to any online platform that facilitates dating between two individuals.

However, the term “easier" is relative. Online dating makes communication between couples easier and faster compared to telegrams and mailed love letters decades and centuries ago. It also opens an opportunity to meet a future mate anywhere around the globe regardless of distance. However, online dating also has its drawbacks which can make dating harder.

Among other things, online dating can set one’s standards too high which will make it harder for someone to look for a match. It can also make someone immediately lose interest in the person they are dating.

The Reality of Online Dating for Some Men

It is easy to meet people online, but it is not easy to keep a conversation or connection with them. Sometimes, you may lose interest in them, and there are also instances when they lose interest in you. Then, the conversation stops, even if one party still wants to keep the conversation going.

It is frustrating to have found someone that you like and to have felt an instant connection with them, but they ended up being uninterested in you after a few hours, days, weeks, or even months of online communication. Or when you want to continue the conversation in order to learn more about them but they already want to cut off the communication.

The worst-case scenarios of these situations are that you end up being ghosted (left hanging without any notice) or being blocked by that woman.

To be fair, most women do not just block a guy online for no reason. If you got blocked, you may have offended them, or you may have made them feel uncomfortable, unsafe, or in distress. Some women, on the other hand, may also block a guy because they are extremely uninterested and do not want to keep the conversation going anymore.

Hence, to keep yourself from getting blocked, you must do two things: check on yourself and understand women.

  1. Check on yourself and reflect on what you are doing wrong, especially if you are experiencing a series of blocks, ghosting, or friend zones. One, two, or three cases may not be on you. But if you are experiencing five or more consecutive cases of blocks, ghosting, or friend zones, maybe there is something that you must change about the ways you approach and interact with women.
  2. Understand women and know how to keep them interested. Put yourself in their shoes and think about what you can do to keep them interested without changing and losing yourself.

7 Tips to Keep Women Interested in Your Conversation and With You

To help you with this, this article will list 7 tips that will help you,

  • understand women better,
  • keep the conversation engaging for both of you, and
  • avoid getting blocked online.

In the long run, these tips may also help you end up in a relationship! The tips may also give you some dos and don’ts while engaging in a conversation with women.

Let’s dig in!

Mansplaining is the act of explaining a certain subject to someone, typically by a man to a woman, in a condescending manner.

Mansplaining is the act of explaining a certain subject to someone, typically by a man to a woman, in a condescending manner.

1. Avoid Mansplaining

Avoid assuming that the woman you are talking to is naive about the things that you know because she may be as knowledgeable as you on the subject. Women today are breaking a lot of women stereotypes and they do not like it when men try to “educate” them on something that they already know as if they do not know it. This is like receiving a piece of advice that is totally uncalled for. Hence, they may eventually lose interest in the conversation if the person they are conversing with is mansplaining.

Examples of common scenarios are explaining to them what certain sports are about when they already know about it, or when trying to explain to them a movie that is commonly liked by men.

The tricky part in avoiding mansplaining is knowing what they already know on the subject that you’d like to talk about, especially if you are still getting to know more about each other. In this case, the key is knowing how to say it or how to start a conversation about it. Consider this example on the topic of black coffee drinking.

Do not say, “I like coffee, especially black, without any sugar or milk. Try it, it’s good. It is good for the body, especially when I work out.”

Instead, say, “Do you drink coffee? I like coffee, and I like it black. Have you tried it?”

The more ideal situation, in this case, is to let them answer the question first before saying your preferences and own view.

In the first statement, it is implied that the person is not drinking black coffee. But what if she is? Then, the information you mentioned is then totally uncalled for, and the subject became about the man alone. In the second statement, especially if you let them answer first, it is implied that you wanted to know about her and that you want to hear her answer. It will be about both of you. Also, if you know her answer, you will be able to know how to pace the conversation about the subject – should you go deeper on it or should you change the topic?

If you worry about unintentional mansplaining, it is safe to always start with a question first when opening a subject. Ask what they know about the subject, their idea about it, or if they ever heard about it.

Self-pity is the tendency to focus on one’s misfortunes and bad qualities. Moreover, self-pity remarks are statements that usually focus on one’s bad qualities and perceived suffering.

Self-pity is the tendency to focus on one’s misfortunes and bad qualities. Moreover, self-pity remarks are statements that usually focus on one’s bad qualities and perceived suffering.

2. Beware of Self-Pitying Attitudes and Remarks

Some guys or men use self-pity to catch woman’s interest in a form of emotional manipulation. They tend to attack women’s empathetic nature to keep them engaged in conversation.

These guys usually express self-pity remarks such as,

  • "This is just me; why would someone like you like me? I’m not even good-looking."
  • "You’re a nice person, you will not like me."
  • "You are better off with other men than me."
  • "I will never reach your level."
  • ... and a lot more.

One or two of these statements may be tolerable, depending on the woman you are talking to, but sticking with this tactic will not get you far with your conversation. Women are not particularly fond of men drowning in self-pity.


Men who radiate so much self-pity may be prone to be blocked online.

Again, some men do this intentionally because they think it really works to get a woman’s interest. On the other hand, others may also do this unintentionally. These men probably don’t know that they are trying to manipulate women emotionally through self-pity remarks.

If you are doing this intentionally, stop. If not and you wonder if you do, check yourself – how you talk to women and how you talk about yourself. Are your statements all about you? Do you talk so much about your misfortunes and bad qualities?

3. Be More Expressive

Women appreciate a man who is courageous enough to express himself and his views.

If you urge a woman to talk about her feelings and emotions to keep them engaged in your conversation and they answer you truthfully, counter it with the same truthfulness and enthusiasm. Likewise, if they open a subject that touches on emotions and a personal perspective, answer them with the same enthusiasm and truthfulness you want to hear from them. Also, feel free to express your personal boundaries with them.

Remember that it is hard to trust someone who cannot express their feelings and views in life. Show them that you are trustworthy by expressing yourself.

4. Talk About Each Other's Interests

Sometimes, the conversation can become so light and comfortable that you unknowingly end up talking about yourself and your interests for most of it. People tend to feel good when they talk about themselves. It happens, and that is okay, but balance yourself as well.

If you tend to feel good when you talk about yourself and your experiences, women do too. So, know about their interests – their favorites.


- Don't overdo it.

- Don’t make it sound like an interrogation.

- If you ask about theirs, talk about yours as well.

To keep the conversation from being all about you or all about her, you can make it about both of you. For instance, ask them a question—for example, about their hobby during their free time—and when they answer, you can share your own interest or views. You can also start by sharing your fondness for something, then ask them about theirs.

Talking about each other’s interests is a good way to know more about one another and strengthen your bond and connection. Also, if you really like the woman and want to pursue her in the future, this strategy will be helpful in the long run.

5. Be Yourself

Cliché, but this will never fail you. Don't try so hard to be someone you are not. If you are unnatural, it will be noticed one way or another.

One of the biggest mistakes of some men, and some women, for that matter, is that they tend to try to be the person they think the person they are talking to will like. In some cases, they even try to be the "perfect" and ideal guy. If you do this, you are likely to lie. After that, you must be consistent with those lies, and that is a lot of work. Hence, save yourself from the work and do not lie. Don’t try to be someone you are not.

Apart from this, lying is not a good foundation if you are to start a relationship. This also includes lying even about small things, such as telling her that you also like something that you don’t (e.g., music, food, a movie, etc.).

Remember, women appreciate men who are truthful and who can express themselves as they truly are. A woman liking you for who you are is a lot better than liking you for who you are not.

6. Be Sensitive

Women always prefer men who are sensitive and understand their feelings. When they feel understood, they may also feel loved, safe, and comfortable.

The problem is, women are sometimes unpredictable—in some cases, most of the time. They may suddenly stop talking to you for no reason; they may get mad or annoyed; they may just be grumpy all day, and you may not have a decent conversation with them. I hear you. It happens, and this is when sensitivity comes in.

Trust me, you don’t want to argue with most women when they are angry or annoyed or lie to them when you are already caught red-handed. A lot is happening inside a woman’s head, and her emotions can be too much to handle. Accept that you won’t understand most of what they are going through because, unless you really try to understand, you will not fully understand.

Biologically, most women are more emotional than men. Why? hormones and how their brain is wired.

Hence, be more sensitive to changes in their mood, their feelings, and even their behavior.

Know when to stop the conversation—they may be feeling tired from the conversation. Also, know when to start it; they may need someone to talk to. And know when to set boundaries for you and her, and respect each other’s boundaries. Do not be too clingy or needy. Both of you deserve time alone for yourselves.

Being a creep or acting like a creep will increase your likelihood of being blocked online.

Being a creep or acting like a creep will increase your likelihood of being blocked online.

7. Don't Be a Creep

Most women do not like to talk to men who use obscene words or who always open a conversation about lewd topics, especially if you are just getting to know each other.

Yes, some women are adventurous and may ride along with this kind of conversation, but do not assume that all women do. Maybe they are not comfortable with that level of a topic while you are still getting to know each other, or they may not be comfortable at all.

If you like to keep talking to that woman, keep a decent conversation. Moreover, if you wonder how comfortable they are with a conversation regarding that matter, you may ask it slowly. Preferably, open a conversation about it once both of you are comfortable with one another and if you have been talking for a long time already.

Hence, if you meet someone online and one of your first questions is about how many times they have slept with other guys before, among other lewd questions, do not be surprised if they block you immediately or after a few conversations.

Final Thoughts

These are simple things that you must remember when you try to start a conversation with women. While the premise of this article starts with online dating, these tips may also be used with your face-to-face encounters with women.

To end, remember that the real key to engaging with women is by understanding them – especially the woman you are engaging with. The tips listed above are generalized among women, but you must know that women are different from one another. Some women are liberated while others are conservative. Some women are adventurous while others are firm and proper. Some may be old-school while others are more open-minded. What works with a certain woman, might not work for another.

If you really want to win a woman’s heart, understand them better and believe in yourself.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2022 Justine Clayre Guiao