How To Keep The Conversation Going On Dating Apps: Matching Energy, Texting Tips, Enthusiasm, Interest. How To Respond, When To Reply (Bumble, Hinge & Tinder) & Penpals

Many folks struggle with app choice, photos, bio, prompts, likes, matches and first messages. It’s not uncommon to never make it past exchanging a few lines with matches. It’s quite a feat to get online dating conversation starters down to start exchanging some meaningful banter, connections and experiences with your matches on dating apps.

The novelty of a new match and person to talk to can quickly dwindle. Repeat conversations can feel like Groundhog’s Day. One can only answer how a day, weekend, week or SIP is going before wanting to rip out eyeballs with mundane, boring generic opening lines on dating sites. Given the number of options people have on dating apps, any cliche, boring messages can quickly lead to you being unmatched or ghosted before you know it.

Below are some tips to continue conversations, transition to date planning and avoid getting unmatched or ghosted prematurely.


How Do You Keep A Conversation Going Over Text, What To Say, Questions To Ask

Now more than ever, it’s tough to keep conversations going long enough before they fizzle out or before a date is scheduled. Nervousness about safety, lack of open places open, crowded trails, streets and parks make it challenging for people to plan dates. Isolation along with job-security can wreak havoc on one’s mental health. Here are some tips to consider not only when matching and after sending the first messages but more so how to prepare ahead of time.

Being good at texting on dating apps and carrying conversation starts before opening the keyboard. It requires you to have enough interests, life experience, hobbies, passions, ambitions, to draw from. The more you stay inside the harder it is to have things to reference, quickly respond to and create banter.

Sure, tv, movies and podcasts help with conversation topics but being current with local and world events, going outdoors in nature and urban walks, having different social circles, trying new local establishments, traveling and exploring (even if locally i.e. new neighborhoods, nearby towns, hiking trails, paths) all help to draw talking points from quickly and easily when you get that match. Having an opinion matters even if you are wrong. No one wants someone who is ambivalent, indecisive, takes too long to reply to or doesn’t get references.


Being Physically, Emotionally Ready For Dating Apps

One of the common mistakes people make is joining dating apps before they are ready. It’s one thing to be emotionally ready from a relationship that ended or being in the right state of mind, but it’s another thing to be socially ready.

Even if both individuals are interested in each other, there is no certainty around what intent means to each person. Dating apps are more like introduction apps – the purpose is to get introduced, spend time getting to know each other and decide if both parties want to meet up.

Nowadays there are many lonely people looking for penpals, people who are taking their time to get to others and of course those that don’t know what they want. Uncertainty and indecisiveness can kill the momentum and raise doubts about sincerity, effort and enthusiasm.


Communication Skills, Social Skills On Dating Sites

Being a good conversationalist requires skills. Often it’s not something one can just wing. A good communicator is one who has a lot to draw from in life, often in terms of experiences such as travel, work, education, hobbies, interests, friends, family, classes and more.

The less one has to draw from the more difficult it is to come prepared to engage in quality conversation. The most interesting people are those that have versatile backgrounds, are a bit of an odd-ball, have varied interests and those that are charming, enthusiastic and convey a healthy dose of energy.

Without energy, effort and enthusiasm, it’s hard to keep conversations going. It’s hard to be excited about someone who doesn’t show and match the same level of these qualities that you possess. Boring, cliche conversation starters get repetitive, especially during covid.

Treating conversations like interviews feel like an extension of Zoom job interviews. Too many people try to play it cool with simple, straight-forward questions and topics but the best conversations are ones that allow both parties to geek-out, be a bit vulnerable and keep the other hooked.

Fear of being one’s true self is an easy way to kill a conversation quickly. Even if a convo dies within a few messages, at least time is saved and both people can move on. There is nothing wrong with letting a conversation die if one or both parties are not interested.


Conversation Starters, Topics For Conversations, Questions To Ask To Keep The Conversation Going

Great conversations involve connections, shared experiences, agreement / disagreement (banter) and/or learning something new. In order to teach someone something new, one has to have the arsenal to be in a position to teach. Being an expert in a variety of fields is a great way to do this. Having strong passions and interests across a slew of areas shows dimension, intrigue and uniqueness.

If someone lacks experience with hobbies, interests, social context, culture, arts or awareness and interest about the world around them, dating apps will be brutal and I generally recommend these people get off apps until they come ready to engage, learn, fail, explore and teach. Dating requires give and take and too often people join apps to fill a void, feel better about themselves, or merely see what’s out there.

Avoid cliche topics or sounding like an interview. Asking a question that has likely been asked hundreds of times is enough for a woman to unmatch rather quickly. Such questions include how is your quarantine going? How is your day? How is your week? How is your morning? These are not bad questions, but they are not great especially if you hardly know someone, and they are talking to other people and hearing the same lines over and over again.

Look at backgrounds and details in photos. Don’t choose the most obvious photo or prompt to comment on. Ask open-ended questions that are relevant to the moment rather than networking type questions or questions that are too random or private. If there is not enough context in the photo but you are familiar with the location, you can inquire about something related to the location – did you go to xyz? what did you think of abc?


Bumble Photos Tips

Bumble Photos Tips For Men, Women



Matching Energy, Enthusiasm, Responsiveness & Etiquette

Don’t waste time or other people’s time on dating apps. Be prepared to give of yourself including time, effort, energy, and vulnerability. A life filled with hobbies, interests and friends will help immensely with one’s dating life. Showing up with nothing to offer is a recipe for despair, fatigue and general miserableness on dating apps. Don’t put all your eggs in one basket, talk to a few people at once and then focus on those you are most interested and want to meet.

Be curious. Ask questions. Provide thoughtful answers. Forget about being cool or polished or proper. It’s ok to be clutz sometimes. It’s normal to make mistakes. It’s fine to be nervous. Online dating (like all things in life) takes practice. Not everyone will be worth your time and that’s ok – that’s why it’s called dating and not arranged marriage. Dating is meant to discover others, what you like, what you cannot stand and what you are attracted to. Dating should be viewed more so like a learning experience rather than an ordering app.

One-worded answers, never being the first to kick off conversations and taking too long to reply are queues one is not interested or at least not worth the time. Focus on those that match your energy. If you don’t have many options to be picky, take a break from dating apps and improve your profile (photos, app choice, hobbies, bio etc.).

Don’t make excuses in your head for others particularly if they never ask. People who are genuine, thoughtful will let you know if they are busy or when they will be free. They will reschedule dates if they cancel on you. Don’t be the one doing all the work. Dating requires give and take.

It’s important to get off the apps asap and not let conversations go on indefinitely as they can quickly fade. One should not match with others if he/she is unable to meet in person within a week or two. When requesting a date, do your research. Find fun places for a date, research alternatives (just in case), consider the weather and location given your date’s location.

Show some effort. Be excited. Don’t expect others to be more excited than you and what you convey through your messaging. Be specific with dates, times and activities. Vague questions get vague answers. 

Broaden Your Interests, Surroundings, Life Experience

Being familiar with an area, going to places alone or with friends ahead of time, being curious, developing interests and figuring out what your match is possibly interested in will go a long way. Writing more about oneself in a bio and through appropriate prompts makes it easier for others to engage.

Hiding details, being vague and providing cliche answers is a sure sign that someone is insecure, not ready to date, boring, or is not going to put in the effort you are looking for. Take queues in the photos, bio, and communication.

When in doubt, volunteer, take classes, explore new routes, dine alone, read the news, make new/different types of friends, check out local culture publications around food, travel, or events. Become a regular anywhere. Talk to strangers. Don’t be afraid to mess up. Those that are not willing to put themselves out there for others signal that they are not ready to meet someone amazing.

Bumble Bio Tip, About Me Section

Bumble Bio Tip For Men, Women, About Me Section


One Word Replies, Delayed Answers + One-Sided Conversations

If you find yourself always the one to start conversations, waiting for replies or trying to draw out the conversation, time to move on. No need to waste your time and energy on people who are lazy, lack effort or don’t match your interest. Some people have a hard time giving up on people mainly due to lack of matches, options.

Don’t settle for less. If this is the case, improve yourself offline and online (photos, bios, app choice, captions, smiles, prompts, appearance etc.) so you can afford to be picky and not settle for losers. If someone is truly busy or going through something, he or she should use good communication skills to let you know what’s going on vs having you ask them. They will make it up to you, express remorse and make plans to correct it and follow through.


How Do You Save A Dry Conversation

If conversations are dead and there is no hope to revive the conversation, be bold and swing for the fences. Some people hate texting, are forgetful or just want to meet in person asap rather than engage in meaningless texts. Be flirty, be forward but be respectful. Randomness, weird observations can sometimes do the trick.


Why Don’t Guys Ask Questions On Dating Apps, Why Do Men Lose Interest On Dating Apps

Some guys start off strong and then slowly fade away. It’s not uncommon for guys to swipe right on every girl and then focus on ones they are most interested in, ones that are mostly likely to hook up with or ones that are most interested in meeting up sooner than later. It’s just one of those harsh realities of online dating.

Your intent with conversation should not be to figure out if he is the one. Your focus should be on qualifying him and seeing if he is worth your time for one date – nothing more. All too often women try to change a man or try to win him over when he has done zero to reciprocate that same effort, enthusiasm, responsiveness, etiquette and commitment. This is precisely why you talk to multiple people early on, keep your options open and don’t think beyond the next date. Related read: Mistakes Women Make On Dating Apps.


How To Keep A Conversation Going With A Girl

When a girl texts you, she is signaling that she is free to chat and wants to chat. If you wait too long, she will message someone else and/or lose interest. Don’t try to play it cool and wait to respond to her. Don’t listen to garbage advice like that. Don’t be overly eager or desperate but be responsive and timely.


How To Keep A Conversation Going With A Guy On Tinder, Bumble & Hinge

The biggest mistakes most women make is not identifying red flags and realizing he is not that into you. Don’t try so hard to start the conversation all the time if he doesn’t match your enthusiasm, effort. Some guys purposely ignore women to see who are the most desperate of them all. You shouldn’t have to chase after someone all the time but you should make it easier for them to strike up conversations by filling out your profile, bio and prompts with more details, anecdotes and examples.


Online Dating Penpals, How To Tell If Your Match Just Wants To Be Penpals: Dating App Penpals

If your match dodges questions about meeting up for a date or declines your date ideas but offers no follow up i.e. alternative days, request for time, you might be wasting your time with a penpal. Most people are comfortable meeting after a few days or at most a week or two depending on availability. If your match offers no timetable for availability, move on. Too much texting before a first date can sabotage any opportunity for something romantic.

Dating Coach Services

First date ideas, wardrobe styling, places to meet singles, where to sit at bars and restaurants, body language, vocal intonation, eye contact, conversation skills, how to flirt over text, how to be more approachable and get people to start conversations with you, mock dates and more.

About Eddie Hernandez

Eddie Hernandez is a dating consultant & professional photographer based in San Francisco, servicing clients in New York City, Los Angeles, Chicago and beyond as featured in the NYTimes, SFGate, ABC7News, East Bay Express, Salon; contributor to Good Men Project, Plenty Of Fish and Meddle.

In addition to photos, he provides guidance around app choice, bio optimization, messaging techniques, wardrobe advice, date planning, screening profiles, ID'ing red flags, offline techniques for meeting people organically, naturally. 

Dating App FAQ's  |  Online Dating Resource Guide  |  How To Be Successful With Dating Apps

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