Tips To Keep The Conversation Engaging When Texting A Guy

Updated September 19, 2023by Regain Editorial Team
“Engaging in conversation over texts can be tricky, but a convenient way to stay connected and show interest. Remember to be yourself so that you present yourself authentically while also trying not to overthink what you send and receive. Remember you are worthy of love and connection. ” - Ryan Smith, LPC, NCC

Texting can be a wonderfully convenient form of communication that offers many benefits. However, texting has some drawbacks too, and it can be hard to keep the conversation going when you're trying to figure out what to say. Read on to learn tips for holding a guy's interest through text messages and how therapy can help you improve communication skills. 

Do You Have Trouble Communicating With Guys Through Text?

What Texting Is Such A Popular Communication Method

Test messaging offers instant communication with anyone in the world at the touch of a button, so it’s no surprise that it has exploded in popularity over the past two decades. Compared to other methods of communication, it is relatively low-cost and offers the opportunity to send messages without interrupting the other person’s schedule as a call would. 

It is important to note that texting has some drawbacks too. Along with texting etiquette (the social guidelines for texting manners), you should remember that text messages don’t offer tone or inflection, and it can be easy to miss contextual clues or make assumptions. Misunderstandings and misinterpretations can frequently occur, so ask for clarification if you need it. 

Benefits Of Texting

  • Offers a direct line of communication between people
  • Many people prefer to text rather than talk on the phone. 
  • Responding is easy and can be done at your convenience. 
  • Cost-effective and accessible in many parts of the world

Monique M. H. Pollmann et al, study of in-person vs. text communication

How Often Should You Text Him?

When starting a new flirtation or relationship with a guy, you may want to text him constantly because he's on your mind. According to recent studies, adolescents send and receive an average of 67 texts daily; between 45% and 65% are texting romantic partners or interests. 

If you're not sure how often to text him, pay attention to how he responds. You should be fine if he's texting back quickly and seems engaged in the conversation. However, if there are long gaps between his responses and he doesn't say much when he does talk, he might be overwhelmed. 

“Text messaging has been identified as the medium of choice for continual relationship maintenance, and text messaging from mobile devices overshadows all other media forms for the support of social connections.” — Exploring Generational Differences in Text Messaging Usage and Habits

Texting Etiquette 

  • Respond to a text with a text. 
  • Don’t be upset if you don’t get an immediate answer. You don’t know what’s happening on his end.
  • Text the same day/night you get their number.
  • Wait for a response before texting again.
  • Take a second to scan your message for typos before sending it. 
  • Balance your use of emojis and exclamation points. 
  • Don’t deliver sad news or break up over text. 
  • Avoid texting under the influence. 

Tips For Holding A Guy’s Interest Through Text

Many guys need help communicating or reading contextual clues through text messages, so don't automatically assume he knows what you mean. If you’ve had trouble keeping the conversation going with a guy you like in the past, try some of these tips. 

Use An Upbeat Tone

Many men appreciate an upbeat tone and a positive attitude when texting someone. That doesn’t mean you have to fake it if you’ve had a rough day, but if most of your texts are negative or don’t offer opportunities for him to engage with you, it may be hard to hold his interest. 

Keep It Simple To Start The Conversation

A little can go a long way when texting a guy. Try sending a simple message like, “Hi, handsome. How’s your day going?” It sets a light, flirty tone, demonstrates your interest, and invites a detailed response. 

Give Him A Reason To Respond

If you only send short or single-word messages, it can make it hard for him to respond. If he asks how your day went and all you say is “Fine,” where does the conversation go from there? You're texting him to start or continue a conversation, which means you need to hold up your end of it too. 

Talk About Common Interests

When you don't know what to discuss, ask questions until you find a common interest. You can even make it a fun game to help you get to know each other. Plan to ask 20 questions in total (10 each) with the goal of finding something you have in common. Each of you chooses how many questions you’ll need to find five things you already share. The winner gets to pick your first/next date. 

Ask Fun, Open-Ended Questions

Keep the conversation going by asking open-ended questions that inspire in-depth answers. You could try asking what he’d buy first if he won the lottery, what he’d change if he could alter anything worldwide with the snap of his fingers, or what role he would play in an apocalypse. 

Make Him Feel Special

Many men enjoy it when you pay attention to them and ask how they’re doing or find unique ways to let him know that he’s on your mind. Texts to wish him good morning and goodnight will likely be welcome, and if you’re thinking of him throughout the day, send a quick text to say so. 

Send Photos To Show Your Day

If you see something that captures your interest or you think he may like, snap a picture and send it to him. If you're feeling attractive, you can snap a quick selfie or send photo clues to hint at a fun date. Adding the visual element to your conversation doesn't have to be remotely sexual. 

Use Sentences Instead Of Abbreviations

Using complete sentences and proper grammar can ensure you convey the message you want without misunderstandings. While teenagers often use abbreviations, "text speak" can be almost another language for people who aren't used to using it. Until you know one way or the other how he prefers to text, take the time to type out your messages and use punctuation. 

Be Witty And Fun

You should convey the same level of emotion, interest, and curiosity through your text messages that you would if you were face-to-face with him. Many men appreciate a sense of humor, so don’t be afraid to make him laugh. 

Ask About His Day

You can show your interest by asking about his day. Instead of asking how it went, try something like, “It’s great to hear from you. Did anything interesting happen to you today?” He may appreciate you showing curiosity about his experiences. 

Match His Message Length

If he sends you a sentence or two, try to match your message length to his. Don’t respond with a paragraph or multiple paragraphs to a quick text—and if he sends a longer message, don’t respond with a short answer that doesn’t give the conversation anywhere to go and may make him feel you can’t be bothered.  

Additional Texting Tips

  • Avoid drama and gossip
  • Don’t be afraid to flirt
  • Use texts to make in-person plans
  • Follow his conversational cues
  • Don’t go overboard with emojis
Do You Have Trouble Communicating With Guys Through Text?

Reach Out For Help

If you have trouble communicating with other people, you may benefit from speaking with a qualified therapist online whenever and wherever you have time in your busy schedule. Therapy can help you learn healthy, practical methods to express your thoughts and feelings while addressing any underlying issues that may be holding you back with the support and guidance of a mental health professional.  

How Therapy Can Help You Build Communication Skills

Many people have difficulty expressing their feelings and needs, making it challenging to carry on a meaningful text conversation. If you have a hard time communicating with other people, consider working with a licensed therapist online through a virtual therapy platform focused on relationships, such as Regain. Parents or guardians seeking help for their children can contact TeenCounseling for online therapy for kids from 12 to 19

According to the most recent data, there’s no significant difference between in-person and online therapy results. However, virtual treatment is often cheaper and has shorter wait times to speak with a therapist. Online platforms also offer access to a much wider variety of therapists, so you have a higher chance of finding someone who fits well with your personality and situation. 


Many people experience difficulties keeping an engaging conversation going over text. The information provided in this article offers insight into some tips to make texting a guy you like smoother and how therapy can help you build your communication skills to make texting easier. 

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