Dating App First Date Ideas, What To Talk About & Where To Go On A First Date, When To Ask For Dates, Coffee Dates, Drinks & First Date Jitters + Nerves, Etiquette & Asking For 2nd Dates

So you have matched with someone on a dating app, managed to flirt your way through not so awkwardly spaced exchanges and are ready to ask the person out on a date – congratulations! Many folks don’t make it this far due to various reasons (wrong app choice, negative/lazy bios, self-sabotaging photos, unrealistic expectations about whom they can attract or poor communications skills).

Online dating can be brutal for many – endless rejection, no responses, lack of likes and matches as well as the not so uncommon ghosting. Online dating requires patience, knowing what you want, thick skin, ability to read people and profiles as well as a bit of luck (liking + swiping at optimal times, selecting the right dating app; hint: not all dating apps are the same, and a bit of luck).


Awkwardness & Transitioning From Online To Offline

For those that have matched with someone they like, the first few messages can be awkward, random, uncertain or dull. Not every comment and response requires a timely witty comeback, sometimes the best approach is being honest and direct with your matches. Places like San Francisco lack men who are direct, candid and show some vulnerability. Knowing your strengths, matches and competition will pay dividends on dating apps as well as encounters offline.

Transitioning from matches to dates is a tricky road and many people assume the latter is a foregone conclusion when that couldn’t be further from the truth. You are competing against time and other people (people your match is dating, has matched with or has yet to match with). Being quick but not overly eager to set up a date is a delicate balancing act where no algorithm nor framework is perfect.

The fact that you have matched with someone is a sign that there is mutual interest. Knowing the sincerity and depth of the interest is hard to figure out. Unless someone gives you a reason not to trust them or take them seriously (negative bios, bathroom selfies, narcissistic photos/bios, short bios and messages, blurry/dark/distant photos) you should give people the benefit of the doubt.

Coming in with a jaded mindset with inability to trust people is not healthy and will lead to problems with dating apps done the road.

Along those lines, you should constantly review people and their profiles and not make any assumptions. Using common sense and not making excuses for others will help keep a healthy outlook on dating.


When To Ask Someone For A Date After Matching, Texting A Girl, Messing A Guy

Most people would argue trying to secure dates as soon as possible is the best approach – this is more likely the case if you are looking for something casual. Many guys looking for something not so serious will suggest meeting that night, for drinks and a place close to theirs on apps like Tinder that are location based.

People looking for something with more of a relationship possibility focus will respond timely, show they have read your profile, will ask you questions, will add depth to replies, will want to get to know you. These are a few of the early signs of showing sincere interest in someone but by no means is it exhaustive. Being patient, spending time with someone in a variety of settings, meeting their social circles will help add confidence during the courting phase.

With this in mind, most folks will exchange somewhere between 3-7 or so exchanges over 2-5 days before setting up a date. One philosophy with some serial daters is to go on many coffee dates or go out for drinks asap.

The thought process here is that dinner or a meal requires too much commitment and time which can be awful if you know things will not go anywhere within the first 5 minutes of meeting. Additionally, few people are commitment phobes and desperately avoid making plans beyond 1-2 weeks.


Date Settings On Hinge Date Ready, Bumble Covid Date Preferences

Thanks to covid, dating apps have instituted dating preferences on dating apps that signal what users are open to for first dates. Bumble allow users to select virtual dates, meet IRL or open to any date. Similarly, Hinge will ask matches if they are ‘Date Ready’ or ‘Date From Home’ indicating if they are ready to go on a date.

You should be aware of what these settings are and plan dates accordingly if not, your match will think you did not read their profile and should immediately unmatch.


How To Schedule A First Date, After Matching, Texting. First Date Locations, Fun Date Ideas

Planning a first date is part strategy, part communication and part luck. Depending on schedules, some people prefer weekday dates after work as to not get in the way for weekend plans. Others prefer weekend dates so that they can relax and have a drink. Knowing your audience coupled with not letting too much time elapse is key for setting up a date.

Requesting dates roughly 3-10 days out is usually a safe bet but it doesn’t hurt to ask for a date last minute if something opens up, a particular one-time only event is happening or if you are eager to see the person. Waiting too long can hurt your chances as it gives the other person more time to match, go on 1st dates and subsequent dates.

A girl has got to eat. Consider the time and pick places that have food as an option but not the main portion of the date. I like gastropubs or restaurants with bar seating. Light snacks are a great, non-commital way to not drink on an empty stomach but without the commitment of a 90-120 minute date for which neither of you will feel obligated to. If you date works a traditional 9-5 job, a date during the week should start no later than 6pm-8pm. You don’t want to start the date too late but want to allow some time in case dates are extended.

Fun Date Ideas: 


How To Confirm A Date Without Sounding Desperate, Needy

It’s not uncommon to set a date far out in advance do to schedules, life etc. When that happens, it’s good to check in and confirm the date ahead of time. Checking in 1-3 days before the date is fine depending on how far in advance you set a date.

A simple message saying you look forward to the date and providing any info with respect to traffic, parking, weather or new menu items is a great way to have purpose without sounding needy or that you expect to be stood up (again). 


Warming Up For A First Date, First Date Jitters, Dress Attire

Waiting for a date to start can be excruciating. Scoping out venues, waiting anxiously, showing up late or having others notice you are obviously on a first date can cause anxiety. Some guys plan ahead and go to the gym workout or a run before to pump themselves up (shower in between obviously). Make sure you are not exhausted from an intense workout either – this could backfire easily if you overdo it on your workout. Make sure to get plenty of rest the night before.

Plan ahead so you arrive in time. Plenty of people rush out the door and worry about showing up late. First impressions are key. Show that you value the person’s time. Similarly, if you are a bit lethargic, consider an espresso or coffee to perk you up before your date. If you are the type that gets hangry, consider grabbing a piece of fruit on your walk over to calm your nerves.

Regardless of timing, dates should be specific (date, time and location) and should allow for wiggle room to end it early in case either party is not feeling it. However, one should always plan to extend the date in the back if their minds in case they hit it off. Improvising, thinking ahead and planning dates around the other person’s interests shows some effort.

Dressing up appropriately for a date can work wonders for confidence as well as conversation starters. Many guys ignore this part of the date planning process especially when coming straight from work (looking at you tech bros in Patagonia vests and company schwag). Show that you put some thought and effort into dates by dressing up.

Don’t over apply cologne (1 spray is fine – clients get my pick for the best cologne to use). Accessories are key and provide a touch of color and flair (dress shoes, socks, scarf, jacket, watch, color scheme and fit are things all women notice). Don’t be another cliche date – stand out, be bold, be confident.


Online Dating First Date Greeting: How To Great Your Date

Most people prefer a short hug. Too long of a hug can feel weird, creepy. A handshake can suggest disinterest. Some people may not feel comfortable with a hug so look out for body language or extending the arm pre-emptively from a distance.

Read More About First Date Greetings During Covid


How Long Should A First Date Last? How Long Should A First Cofee Date Last?

Dates should be at least 30 minutes but should allow for extra time in case things go well and both of you want to extend the date. This can mean grabbing drinks at a bar area of a restaurant and ordering another round if you both are up for it to grabbing a small bite.


Are First Dates Usually Awkward?

Yes, it’s not uncommon for first dates to be super awkward. This is especially true if you don’t look like your photos, don’t have a lot of dating experience or are too on edge and nervous. Over time, people typically become more comfortable with first dates unless they don’t know how to act, are not themselves, are too reserved and end up too concerned about getting rejected again and again.


Where To Go On, How To Act On A First Date: Hinge, Bumble First Date Tips, Coffee Dates

As I mentioned above, date places are crucial and can make or break you. Offering to meet someone on a time window around their schedule can show interest and flexibility even if it is for a quick 30-minute coffee date. Dates that require planning, distance, changing attire should all be taken into consideration and weighted appropriately.

Coffee dates are efficient, low effort and low risk dates options. They are also hard to develop chemistry and rapport depending on the environment, time of day and limiting options nearby. Having a place to walk around and explore during or after coffee should always be planned but never assumed if you have not made definitive plans.

Researching events or other one time offerings nearby via Eventbrite, Newspaper, Eater etc. can provide an easy way to extend dates, add movement and versatility to otherwise stagnant coffee dates. It pays to keep tabs of things in your area in your back pocket at all times. Stalling for ideas on Google or Yelp apps kills momentum.

Drinks are another easy way to get to know someone quickly and easily. Some people need a little liquid courage to loosen up. Others do better in more fluid environments with good people watching possibilities. Dates can last as little as 30 minutes or last long into the night – that flexibility is great for dates that you are uncertain about.

One thing to consider is location. Some people are protective of their favorite venues, bars, restaurants etc. Places nearby homes and workplaces can be awkward on first dates due to the likelihood of running into someone you know.

Conversely, selecting places far away increases chances people may need to reschedule or cancel dates because of timing. In either scenario, having back up plans due to time constraints, private events and weather shows extra thought and effort in case things go sideways.

Pro-tip: Most people have access to taxis and car-hailing apps but it helps to be thoughtful and plan dates near public transportation and in good (not so seedy) neighborhoods.

Sitting Next To Your Date vs Sitting Across From Your Date: Face To Face vs Side To Side

Sitting next to a date or sitting across a date is another thing to consider. I am not a fan of sitting across a date for long periods of time, especially at booths or tables. It can be too much to endure for a first date. I prefer sitting next to or sitting at the corner of the bar (it removes extra space in between you – the table). This allows each of you to turn closer to each other or get closer if you are vibing. It also adds elements of other interactions and people watching (conversations with patrons next to you, dialogue with the bartender, analyzing other dates etc.)

Some dates might feel shy or strongly about one thing or another so it’s good to check in and ask. A simple ‘ do these sats work for you’ is suffice. Additionally, you may also want to consider small things like waiting for your date outside to avoid the awkward hello inside the bar. Usually a warm, simple yet enthusiastic hug is normal for a first date (it sets the tone). Seats next to the front door might be drafty so consider that. Sitting 45 degrees to each other is a great way to start off a date without having to be locked into each others eyes 24/7.

Dates should always be analyzing each other to see the other person’s manners and etiquette. Do you they you into your seat? Do they help place your coat on the back of the chair? Do they ask to see a menu from the bartender or ask to borrow the menu from the patrons next to them? Did they research the place on Eater to see what is recommended? Do they ask to see what the date likes (ideally this is discussed before the date but if not now is a good time).


Topics To Discuss and Topics To Avoid On First Dates

Sounding negative, discussing past relationships and marriage and children plans are generally frowned upon on first dates. Some folks would add politics and religion to that mix but in this day and age, those are a little easier to navigate at least indirectly.

Conversations should be a balance of open-ended questions and answers, stories and examples, observations, curiosities, passions and aspirations. If it feels like an interview, either change course or abort the mission.

It is imperative that you are well-rounded enough before you go on dates or you can expect conversations to go stiff quickly. Food, travel, work are cliche and grow stale quickly. Discussing weekend plans, holidays, current events are a bit more spontaneous, relevant and require non-rehearsed answers and insights.

Being able to talk about more serious items can be a good thing as long as they are not too intense. Providing a deep conversation that allows both of you to open up with some emotion, strong opinions or some vulnerabilty can make or break you in a good way. Often times, dates that play it safe get stiff and become boring. Hot takes are a good way to see where you date stands on certain issues but make sure they are not cliche or seem rehearsed. Spontaneous, go with the flow and super weird, peculiar or random insight is a great way to connect with your date.

Pro-tip: Some places are more conducive for first dates i.e. places that don’t require awkward eye contact across the table. Finding creative seating environments can make or break a date.  Some seating arrangements make it easier to hear each other, allow for breaks in eye contact and allow for introduction for third parties like servers, bartenders or nearby tables to add elements to conversations.

How To Keep A First Date Conversation Going

It’s all about dressing well, picking the right date spots, knowing where to sit, having the right topics to discuss as well as being present, excited and approachable during your date. In addition to these first date logistic items, you also have to know how to choose who to go on dates with (not everyone is worth your time) and have enough to talk about.

Traveling, taking on new hobbies, living in different areas, surrounding yourself with interesting people, trying new things out and communicating emotion and vulnerability are key. You can’t fake this. You can’t hack this. You have to know how to live a good life in order to speak to it. If you are boring, dull, work too much, have a boring job, live in a boring town, don’t have friends and don’t go out much, dating will be brutal.

Should You Go Dutch On A First Date? Who Pays For A First Date? Splitting The Bill On A Date

First dates should be casual. Avoid fancy dinners or expensive activities. One should expect to pay for the first date if he/she asks the other person out. Similarly both people should expect to split the bill and pay their way. This is why I suggest drinks or something casual rather that something elaborate.

If a woman accepts a date, it’s customary to split the bill especially if there is no chance of a second date. With that said, a woman may want to pay her own way so that there is no doubt about something being owed or her going out on a date for a free meal (it’s a sad, pathetic way one has to think about this but there are many jaded men who think like this).

As a woman, if you want to see the guy again and he insists on paying for date #1, suggest you pay for date #2. The way people respond to bills at the table says a lot about them and their intention. As a guy, you should know how a date is going but you could say you will pick up the check this time and will let her pay if she decides to see you again for date #2.


Exchanging Phone Numbers + Asking For Second Dates

Most dating apps work perfectly fine for communication – no need to take things offline to WhatsApp, Text or Snapchat especially before meeting. People can research phone numbers and find additional info about you so there is that to consider.

As a guy, I recommend providing a phone number in advance of the date (after it is secured) to reduce chances of unmatching, app glitches etc. On the same note, asking for a phone number before meeting can be seen as too eager and unnecessary as referenced above.

I recommend asking for numbers at the time or after a second date is secured. This is not always a guarantee but possesses a strong chance. Creating new contacts, syncing profiles to contacts and confusing folks based only on their first names can be tedious.

Second dates should always be requested at the end of the first date. Any delay can suggest uncertainty and no one wants that. Ambiguity kills relationships. If you don’t make your intentions clear assume others will.

Having specific plans for a second idea is helpful (especially if you discussed hypothetical dates during the first date) but leaving it open and mentioning planning something specific next day (in most cases) is fine if you are at a lost.


Virtual Dates, Zoom & Skype Video Chats

Video chats and dates can be tough – dark lighting, weird angles, unflattering backgrounds, what to discuss and talk about during quarantine. I wrote about my thoughts about dating during Covid-19 below. I do think people should wait given heightened sense of boredom, looking for entertainment and loneliness but if you must use dating apps, read this article about dating during the pandemic.

Unmatching Before The First Date (Hinge, Bumble & Tinder)

It’s not uncommont for guys to unmatch before the first date. It seems weird or rather odd and while it could be an accident or could be he deleted his profile, some guys do this to make it harder to report them if the date goes bad. This is a possible red flag to look out for when going on a date.


Updating Dating Profile After First Date, While Dating

After a first date, you might be wondering how the other person feels. It’s not always clear if the


Hinge We Met Survey: What Happens If You Say We Met On Hinge

Hinge follows up on people to see if they went on a date with their match and if they would like to see them again. They claim to use this info to better serve matches (false, in my opinion) but mostly to gather data for reporting metrics for PR purposes.

They can tell if you went on a date based on location-tracking, proximity and amount of time your phones are close to each other. Hinge will likely serve you the same people, slightly different order but their main focus is monetization and doing an adequate job to not get you to leave the app.


How to Keep A First Date Conversation Going

The ability to carry a conversation depends on who you are on a date with, your own life experience, how eager they are to talk to you, ambiance, nature of the date, surroundings, time of day and where you are seated. Bar seating provides a great view of the bar, ability to watch drinks being made and opportunity to people watch.

Your life will be the biggest indicator on how well you can carry a conversation. If you don’t get out much, don’t have many hobbies and don’t do much in life, it will be hard to fake anything. The more you do, the more you have to talk about. Seek questions that are relevant to the moment, are open ended and provide opinions, insight or personal experience. Don’t treat things like an interview, be vulnerable to allow others to be vulnerable as well. Learn to listen vs waiting to speak. 


How To Create A Spark During A First Date

Fun date ideas create the best opportunities for a spark to occur. Music, movement, people-watching, a connection built by great conversation, self-deprecating humor, vulnerability can all help create a spark. Being too guarded, acting self-conscious, lacking depth in answers to questions and failing to be curious about your date can make it difficult to create a spark. Boring dates, lack of emotiona and vocal intonation are reasons why some people find it hard to create a spark.


First Date Spark – Does A First Date Need A Spark? Does No Spark Mean No Attraction?

Sparks on first dates are not always needed. Some people expect a fair tale first date either because they see it in movies or one of their friends experienced it but most relationships don’t have a first date spark. The purpose of date #1 is to figure out if there will be a date #2. Some people demand it but that is mostly due to insecurity.

Change up the second date, make your desire to go on another date known before the date ends and again when you part ways on the first date. Some people have bad days, some are nervous or feel uncomfortable (venue, noise, outfit selection), others are tired or are just not themselves. Don’t take thinkgs personally. Being patient, communicating well and being present and connected is just as important.


No Chemistry On First Date – Can A Spark Develop Over Time

Sparks can definitely be triggered on dates #2, #3. Some people are reserved and don’t want to get their hopes up. If someone is interested in you and makes the effort to treat you well, be attentive and be curious about you, go on that second, third date. Some people need a little assurance to make their feelings well known.

Others might be playing a guessing game as they might be waiting to see how you feel about them resulting in a possible stalement. If you meet a quality person, don’t be shy. Make a move. F gender norms. The only thing worst than being rejected is letting someone get away becuase you were scared.


What To Say After A First Date

Say you had a great time and would like to see the other person. Not all women feel safe declining a date on the spot so it’s not unheard of for a woman to change her mind or be unenthusiastic about date #2. 


What To Say To A Guy After A First Date, What To Text A Guy After A First Date

If you are uncomfortable being direct that is percfectly normal, fine. If you had a hard time being yourself on a first date but want to see him again, you can follow up the date with an indirect text. Stating you had a great time and thanking him for a drink, meal is more than plenty to nudge a guy to ask you out again (assuming he is interested).


How To Get A Second Date With A Guy, Girl

A guy or girl needs to feel some attraction and interest throughout the date in order to be open to a second date. One can do this by making the other person comfortable, choosing a good first date idea, expressing emotion, varying vocal intonation, being present and dropping subtle indirects hints about a possible second date.

By the time a first date ends, there should be no doubt about a second date happening or not. If you are quiet, reserved, don’t initiate conversations or treat date #1 like an interview, don’t expect anything. Be sure to ask for a second date with enthusiam at the end of the first date or slightly before when you have the person’s attention. Sometimes taxis or buses can rush the end of dates so plan ahead, wear a watch.


Canceling Before A First Date

If your life is so busy, unpredictable that you constantly have to cancel plans, meetings and dates, you should not be dating. You shouldn’t double book yourself nor cut things too close. Always leave room for dates so you don’t have to rush, don’t have to worry about being late. If you must cancel, do so they day before rather than not being sure the day of. If you do have to cancel, it is up to you to apologize, reschedule if possible and make it up to the other person.

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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