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Dating in the Digital Age: Advice from an Elder Millennial

By Keeley Teemsma English



Hi everyone, my name is Keeley. And I am old.  Okay, not that old. But old enough to have had a rotary landline in my home and old enough to remember when 347 first became a NYC cell phone area code.  I didn’t get my cell phone until college and it was a pre-paid ginormous Nokia, like legit. And I only got it because 9/11 happened in the second week of the semester that year (yes, 2001) when I was in college.  I barely turned the damn thing on. I got a Blackberry when I was 28 and finally an iPhone when I was 29. Yes, I am old.  

Back in the day (think: pre-2013) online dating was a different ballgame than it is now.  Online dating actually involved quite a bit of work and careful thought. Don’t get me wrong–there were still weird messages, messages that were quite obviously copy-pasted, and misogyny, but far fewer dick pics.  

So you might be asking yourself, “how is this elder Millennial qualified to school me on online dating?”  Because I did it. For quite some time. And I had good results.  

I met a lot of great people who were invested on going beyond one date.  So there is a method to my madness.

Yes, I met my husband on OKCupid.  Our first date we met up for a drink.  We had a lot in common, he was a native New Yorker like myself, was employed full-time, lived alone, and was wrapping up a master’s degree.  He hit most of the items on my would-be checklist. I thought he was nice, he didn’t creep me out, and I didn’t feel like I needed to pretend around him.  The conversation flowed well. But I didn’t feel any “chemistry.”  

He asked me to go out again, which I wasn’t expecting, but since I was fairly certain that he wasn’t a sociopath and being that we did have a lot in common, I accepted and we went out for brunch.  I thought he was nice, albeit nervous, but we had a good time. I made a point of keeping my expectations low, and again, didn’t anticipate that we would see each other again. He stayed in touch though and it was on our next date, over tapas, that things really clicked. We were both able to have fun and something felt different. 

In short, my husband didn’t meet 100% of my “perfect partner” criteria at the time, and had I given up after the first date or two or simply because he wasn’t exactly perfect, I would have missed out on being with a really great person. 

The number one complaint I get in sessions is about the state of online dating as it presently is.  It is important to know that dating apps weren’t designed with your best interests in mind, they were designed to make money.  They were designed to get the users (i.e. you) addicted to them so that you will spend more money. We believe that spending the money will get us more swipes and therefore more matches, or perhaps higher quality matches.  But nothing could be further from the truth. The success rate of today’s dating apps are actually far lower than the dating sites of my day.

Using a cell phone is addictive in its own right.  The glow from the screen triggers dopamine, which leads us to feel energized. Any addiction is actually 100% of an addiction to the substance itself, but also to the dopamine.  And dopamine has a very short half-life, so the second you put your phone down, the brain starts to go into withdrawal. Withdrawal is uncomfortable, thus it makes us want to pick up our phones again.  Having notifications on our phone whether it be banners as we are using it or lists on the lock screen trigger anxiety. To alleviate that anxiety, we check our phones. But dopamine is bad for anxiety because it is stimulating.  So it becomes a vicious cycle. Factor getting matches into the equation and dating apps become a powerful addictive force because a great deal of it fuels self-esteem and confidence. 

The reality is that nearly everyone in New York City uses these apps, so it’s difficult to meet people otherwise.  I’ve heard from many people that it is almost seen as weird to strike up a conversation in public with someone you don’t know.  So what I’m proposing is to not get off the apps altogether, but to take measures to make them more productive for you. 



  • Make a list of the must-have qualities you would look for in someone who you’d date. From there, separate your list into 2 columns:  things that are must-haves and things that would be nice but aren’t necessarily deal breakers.
  • Make a list of deal breakers. From there, separate that list into 2 columns: absolute no-no’s and things that you could probably live with if the desirable qualities outweigh the undesirable qualities
  • Write out a list of your values.  And by values, I don’t completely mean items like art or culture.  What I’m really getting at are things that speak to someone’s character.  If you write a list that takes less than 5 minutes, you’ve done this incorrectly.  Take 20 to 30 minutes and dig deep. Then repeat this the next day. 
  • Take some time and really think about what you are looking for.  Are you looking for a long term relationship? Are you looking for a partnership? Are you looking for now or are you looking to be with someone for years to come? Don’t be afraid to make others aware of what you’re looking for.  When you message a potential match, be sure to ask this before you even schedule a date. You don’t want to waste anyone’s time, and I’m sure you wouldn’t appreciate your time being wasted.  
  • Once you’ve done this, go back and re-read what you’ve written and shift items written in the negative to the positive.  For example, “should not be a smoker” would change into “I would like to date a non-smoker”. Or, “I won’t date anyone who hasn’t finished college” into “I would prefer to date a college graduate.”  Use this as a jumping off point in re-writing your profile. No one likes a negative nancy. #Sorrynotsorry.


Understand that no one is perfect

  • You’re not perfect. Neither is anyone else. 
  • There’s no such thing as a perfect match.  
  • Stop comparing your exes to the people you meet in the present.
  • Stop comparing the people you meet to storybook happily ever after romances. 


Put away your phone

  • One of the rudest and most disrespectful things you could ever do on a date is check your phone.  Unless you are a surgeon or other health care provider who is on-call 24/7 or you have a minor child at home, there is zero reason why you should check your phone on a date.  Put the phone on do not disturb (not vibrate!) and don’t take it out again until the date has come to an end. 
  • Don’t check your dating apps while you are on a date, even if that person has left for a few minutes to go to the bathroom.  It’s a super tacky thing to do and is very easy to find out the last time someone checked their app.


Give it some time

  • Go out on more than one date (unless the other person seemed like a terrible person on the first date).  See the other person in the evening as well as in daylight. 
  • Consider dating one person at a time as a way to get past the need for instant gratification. 
  • Try reading profiles before taking a close look at photos.  
  • Don’t give up.  If you really want to find love, you can’t call dating quits because you met a couple of bad apples.  Use the same amount of effort that you would use to find a higher paying or more fulfilling job.  


Be Considerate

  • First and foremost, this ghosting shit needs to stop.  Like now. Show some respect and message the other person to let them know you weren’t feeling it and that you wish them the best.  Give someone (and yourself) closure. Sadly, ghosting is a big contributing factor to anxiety in dating. (And if you’ve ever wondered why I’ve listed a ghosting clause in Refresh’s Termination Agreement, its because ghosting is not acceptable in any situation, is completely disrespectful, and having a termination conversation with your therapist sets you up for being able to have tough conversations when dating).
  • Do not send unsolicited dick pics. Ever.  This conveys a complete lack of respect for others.
  • If someone tells you they aren’t interested, respect their decision.  Don’t make a case for why the two of you should see one another again.  If you have to convince someone to date you, they are not going to respect you.  And don’t be an asshole to them either. Let it go. 
  • Respond to calls and texts in a reasonable amount of time.  If your response time is more than one day, you don’t respect the other person and if their response time is also more than one day, they don’t respect you.  
  • Don’t call or text first thing in the morning.  Doing this adds a layer of stress that many people just don’t want before they’ve had their morning caffeine. 
  • Don’t bombard others with multiple calls, texts, or other electronic communications.  Wait until you’ve received a response to your initial outreach before reaching out again.
  • Understand that many people have work/school/other obligations and may not respond right away.  This is a great opportunity to practice some CBT skills before you stress about not getting an immediate response.


Do some work on yourself

If you think everyone else has a problem and that you’re not doing anything wrong, think again.  If you say things to yourself such as, “all girls want a guy who treats them badly” or “guys are only interested in sex,” you’re not only making a very dangerous generalization but you’re self-sabotaging yourself in the dating world, but also in your own optimism and mental health. Yes, some people are just looking for casual hook-ups or summer flings.  And that’s fine if they are. It’s also fine if you’re not. But you do need to be upfront and ask what someone is looking for sooner rather than later. 


Understand that you are the common denominator in your dating life

Understand that everyone out there isn’t terrible or non-committal, but that you are doing something that’s not working to your benefit. You can’t control others. What you can control is your mindset and the way you interact with others.


Put forth some effort. 

Do you recall the hard work that went into things like writing term papers and getting that promotion at work? Had you done nothing, you wouldn’t have received a grade and if you had sat on your butt and surfed FaceBook all day you wouldn’t have been taken seriously when you applied for that promotion.  The same goes into dating. The love of your life isn’t going to fall out of the sky, and you shouldn’t expect anyone to stick around if you’re not putting in a reciprocal amount of effort into the relationship.  

  • You can’t simply just wait for a compatible match to magically find you.
  • To make this work, you’re going to have to thoughtfully message people on dating sites and apps.
  • You’re going to have to thoughtfully plan every other date you go out on with someone.  
  • You’re going to have to remember the things someone discusses during conversations. 
  • You’re going to have to call/text/email people back within a reasonable time frame— like within a couple of hours.  And if you’re super busy with work, it takes less than 30 seconds to type, “I’m super busy at work but I’ll give you a call tonight after I get home.”
  • Address your reservations about dating, fears, and social anxiety.
  • Self pity is not your friend. 
  • Consider some realistic ways to boost your confidence.
  • Shower every day. Wear clean clothing every day.  Groom yourself every day. Brush and floss your teeth every day.  This will help to improve your confidence, in addition to smelling nice in the presence of others.
  • Stop harping on profile photos and physical attributes.  This an excuse (or what therapists might consider a defense mechanism) for not wanting to put forth effort.
  • Understand that dating has nothing to do with luck whatsoever, and everything to do with the effort you put forth and the choices you make.
  • Ask others questions about themselves, their experiences, their thoughts, and their values.  Don’t talk about yourself the entire time and not learn about the other person, as you might not make it to a second date. 


Rework your profile

  • Have a trusted friend read over your profile and give you honest feedback about what they would think about it if they randomly came across it on their own.
  • Have someone proofread it for spelling, typos, and grammatical errors.  Lots of errors may imply that you wrote your profile in a slapdash fashion and that you aren’t taking dating seriously.
  • Post a variety of photos that you feel confident about. 
  • Don’t post negatives in your profile.  Negative profiles are draining to read.
  • Add in a little humor.  No, your profile shouldn’t be like reading a script for a comedy act. But a little laughter ain’t gon’ hurt nobody!  Avoid self-deprecating humor. 
  • Make it crystal clear that you are looking for a relationship and not a hook-up. 
  • Add enough about what you are looking for without writing something of a length comparable to The Odyssey.  If you’re uncertain whether you’ve written too much, have someone reread your profile for you.


Keep your negative thoughts in check and stop making excuses. 

Have you ever said any of the following?

  • Dating feels like too much work.
  • I’m too old to be dating, I should be married by now.
  • They’re all serial daters who aren’t looking for something serious.
  • Everyone just wants to hook up.
  • I’m unhappy with the quality of matches.
  • We have too many options and everyone is just looking for the next great swipe.
  • No one responds to my messages.
  • Women are looking for free meals.
  • All they do is complain about bad dates, ex’s, work, and money.
  • I wasn’t in love with this person.  I should know whether I’m going to fall in love with someone on the first date.


These are all excuses.  And the “all or nothing” type of thinking illustrated in the above examples can lead us down a dark hole. Remember: you can’t change others, you can only change yourself.


Switch from the Scarcity Mindset to the Prosperity Mindset.

Though this comes from finance, it is a mindset that can be easily applied to other areas, including our mental health and dating.  Be the optimistic person you’d like to meet. Start to redirect your thoughts into some of the following:

  • It’s nice to be able to meet so many new people.
  • Everything doesn’t have to work out.
  • I’ll plan a fun date to go on. 
  • There will be plenty of opportunities to meet lots of awesome people, so it’s okay if one date isn’t fantastic. 
  • Its okay if people don’t message back right away. Everyone has work, school, and social commitments and may not check their inbox all the time.
  • I will go to therapy to be able to better cope with my fears about dating and social anxiety.
  • There is no such thing as bad luck, only bad choices and using this as an opportunity to learn from your bad choices helps you grow.

What are your take-aways from this post? For me, I would say the key points are:

  • Decide what you are looking for and don’t be afraid to make that known early on, or even before you meet someone in person
  • Be invested in going on more than one date
  • Make an effort
  • Maintain optimism
  • Reframe/replace negative thoughts
  • Don’t stress about things that aren’t within your control
  • Love yourself and recognize your self-worth


Let me know your thoughts.