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 Guide

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).

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

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.


How To Schedule A First Date, After Matching, Texting

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. 


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.


Where To Go On, How To Act On A First Date, Face To Face

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.

Topics To Discuss and Topics 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.

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.

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.

About Eddie Hernandez 

Eddie Hernandez is a professional photographer specializing in natural, candid online dating photos. Featured in the 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 and date ideas.

Dating Profile Critique

For those of you who are remote or virtual dating help and are looking for an online dating profile critique you can read more about my services here.

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Online Dating Frequently Asked Questions (Photos, App Choice, Wardrobe, Messaging, Bios and More):

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