Digital romance has become the norm. According to the Pew Research Center, roughly 23% to 30% of U.S. adults currently use or have recently used dating apps, with usage peaking among younger demographics. Roughly 37% of Americans have used an online dating site or app at some point in their lives. While usage is high, especially among those under 30 (53% lifetime usage), satisfaction levels vary, with many users reporting frustration.

While corporate giants like Hinge, Tinder, and Bumble dominate the dating app world, the primary challenge has long been securing the match. Once the notification pops and two profiles align, however, a new, often more daunting phase begins: the conversation. 

It is precisely this post-match anxiety that Shrikrishna Joisa, a New York City-based software engineer and AI specialist, aims to address with his latest venture, AskCupid.

AskCupid is an AI-powered dating coach that Joisa designed not to automate romance, but to assist users in navigating the nuanced, often stressful world of text-based communication. 

Joisa specializes in AI and machine-learning-driven systems at Tata Consultancy Services, and here, AskCupid represents a shift in how technology is used in dating apps. Rather than focusing on algorithms that determine who you match with, AskCupid focuses on helping users understand what to say next. It really is a coach, like an angel on your shoulder, that guides you through the process to see if your current match is aligned with your own communication style.

Dating Apps: Identifying the Friction Point

While the top dating apps in the US have perfected the art of the introduction, Joisa believes they leave a significant gap in user support. “I started AskCupid because most dating apps are optimized for matching, not for helping people navigate what happens after the match,” he explained. “A lot of users—especially those who are thoughtful but not naturally confident—get stuck overthinking messages, misreading signals, or not knowing how to move conversations forward.”

From his own experience and discussions with friends, Joisa identified that the biggest frustration in online dating isn’t a lack of options, but rather a surplus of uncertainty. “People ask questions like ‘What does this reply mean?’ or ‘How do I respond without sounding awkward?’” Joisa notes. “There’s also a real communication gap for users who are dating in a second language or struggle to express tone clearly over text.” That’s especially the case for the apps that don’t have a video chat function or an option to audio record a voice message, forcing users to excel in the art of the text message to secure a date.

Bridging the Communication Gap on Dating Apps

Joisa created AskCupid to address these specific gaps by offering real-time, context-aware guidance. The platform focuses on three core areas: communication, interpretation, and decision-making. The goal is to help dating app users understand messages they receive, craft responses that feel natural, and decide how to move conversations forward without overthinking every step.

A major focus of the AI is tone and intent, notes Joisa. Text-based conversations are notoriously prone to confusion, due to the absence of body language and vocal inflection. AskCupid helps users decode subtle signals, clarify mixed messages, and avoid coming across as either too eager or too distant.

“Text-based communication leaves a lot of room for misinterpretation,” Joisa said. “AskCupid helps users decode subtle signals and avoid coming across as too eager or too distant. It also supports users who may be dating in a second language by helping them express their thoughts more clearly while preserving their original intent.”

Decoding the Dating App Hidden Signals

One of the most innovative features of AskCupid is a category devoted to “Decoding hidden signals.” This feature was born from observing user behavior in online communities, particularly on platforms like Reddit, where users frequently crowdsource advice on interpreting ambiguous texts. For example, The Online Dating group on Reddit currently has roughly 300,000 weekly visitors, and many ask other group members to help decode a dating app text message, while the Texting Theory group has roughly 2,000 posts a month, and mainly focuses on “opening lines” on dating apps, especially Hinge. In other words, everyone needs help with a second opinion with dating apps. Not everyone can figure it out.

“Small things—like delayed replies, short messages, emojis, or sudden changes in tone—often lead users to assume the worst, even when there may be a simple explanation,” Joisa notes. “The same questions came up again and again: ‘What does this mean?’ or ‘Am I reading too much into this?’”

The “Decoding hidden signals” feature is designed to slow down the user’s emotional reaction and replace guesswork with context-based interpretation through the help of AI. The goal is to help users separate meaningful signals from noise, allowing them to respond with clarity, rather than anxiety.

Navigating Stumbling Blocks and Ghosting

Ghosting and the uncertainty of non-responses are among the most common complaints in the dating world. Joisa notes that while ghosting is prevalent, the ambiguity of a non-reply often causes users to disengage prematurely or second-guess their self-worth. 

Ghosting is so prevalent in modern dating, that roughly 60%–75% of users report having been ghosted, and about 45%–50% admitting to ghosting others. It is most common among Gen Z and Millennials (84%), and is frequently cited as a primary cause of dating app burnout, according to a report from Forbes.

“One of the biggest stumbling blocks is uncertainty,” Joisa explained. “Ghosting is common, but often users don’t know whether a lack of response means disinterest, timing issues, or something else entirely.”

Beyond ghosting, users frequently struggle with the momentum of a conversation. The transition from casual texting to asking someone out is a critical juncture that often causes hesitation. “Many users struggle with questions like ‘What do I say next?’ or ‘When is the right time to ask someone out?’” Joisa said. “They don’t want to come across as pushy, but they also don’t want the conversation to stall indefinitely.”

Success Through Clarity, Not Cleverness

Despite being a relatively new entrant, AskCupid has already garnered feedback from users who have found success through the platform. Joisa emphasizes that the most impactful stories aren’t about dramatic transformations, but rather small moments of confidence.

“Users often share that AskCupid helped them send a message they would have otherwise overthought or avoided, which led to conversations moving forward, instead of stalling,” Joisa said. Timeliness is key, too. If you keep a match waiting, it could be seen as disinterest, so AskCupid comes in handy for problem-solving on the spot.

Joisa says that success on the platform is defined by clarity, rather than proving one’s own cleverness. By providing neutral, context-aware feedback, the AI helps users ask someone out sooner and more naturally, preventing the loss of momentum that often comes with waiting too long, for example. “When users feel more confident in how they’re communicating, interactions tend to feel more relaxed and authentic,” he said.

The Intersection of Engineering and Empathy

The creation of AskCupid is rooted in Joisa’s professional background. As a software engineer in New York City, he specializes in designing and deploying production-ready AI and machine-learning systems. His work focuses on translating advanced AI techniques into scalable, reliable systems, a skill set that proved essential in building a real-time communication assistant.

Joisa’s expertise is backed by a strong track record of innovation. He has contributed to multiple U.S. patents granted by the United States Patent and Trademark Office (USPTO), with innovations spanning sentiment analysis, document summarization, and information extraction from unstructured text data. His patented work has been recognized through internal awards for technical excellence.

In addition to his professional role, Joisa independently develops publicly accessible AI platforms. Beyond AskCupid, he created OpenSpeechAI, an AI voice and conversational platform. These projects reflect his ongoing focus on applied AI, combining backend systems, model integration, and modern web interfaces into cohesive, production-ready applications.

A Different Approach to AI and Dating

The integration of AI into dating apps is a growing trend, but a lot of it is not authentic. Joisa believes AskCupid occupies a unique niche. While many apps are using AI to improve matching algorithms, profile recommendations, and safety features, AskCupid approaches the technology from an unlikely perspective.

“We are seeing early experiments with AI-generated prompts, icebreakers, and profile optimization,” Joisa noted. “AskCupid approaches AI from a different angle. Instead of focusing on who gets matched with whom, it focuses on what happens after the match.”

While some platforms use AI to optimize engagement or retention, AskCupid uses it as a support layer for users. The goal isn’t to automate dating, but to reduce uncertainty and help people communicate more clearly and confidently in a space where small misunderstandings can easily derail genuine connections.

Future Expansion: Helping Matches in Real-Time

Looking ahead, Joisa plans to expand AskCupid with a strong focus on utility, rather than novelty. One area of growth is deeper contextual understanding, allowing guidance to become more personalized over time as conversations evolve, while still preserving user intent and authenticity.

Overall, the goal of this potential feature would not be to automate conversations, but to support users in expressing themselves more confidently, especially in situations involving language or cultural barriers.  Every expansion will stay aligned with the core idea of AskCupid: reducing uncertainty and anxiety so people can connect more naturally, without feeling scripted or artificial. In a digital world often criticized for being transactional, Joisa’s AI coach offers a refreshing perspective: technology that helps us be more human.

“I’m exploring ways to reduce friction at the moment people are actually typing,” Joisa revealed. “One potential direction is an assistive keyboard experience that offers optional, context-aware suggestions around tone or clarity while a message is being written.”

Check out Ask Cupid AI at askcupidai.com.