Confessions of a Late 20-Something: Dating in the 21st Century

Welcome to a new yet short series I wanted to do as a way to close out my twenties and pass on some valuable advice. I’ll talk about dating, body image and self-esteem and the working world from a female perspective.

This will be a 3-part series and will last only until the end of 2018.

Why only until then you might ask?

Well, in just 2 months, I will cross over into a new decade: my 30s.

Who says you really have to grow up?

It’s a little bit scary to type that out on paper so to speak but they are literally just around the corner for me. My twenties have been hands down my best decade and they have largely been full of things I’ve wanted to do or places I’ve wanted to go. It’s truly the decade where I not only found my voice but my home abroad, my purpose and my passion in life.

But, before I embark on a new decade, I wanted to pass on some advice I’ve learned through my own life experiences to those who will still be going through the trenches and navigating these very formative years.

So, without further ado…these are my unedited thoughts on love and dating in the 21st century – after years of trial and error and now one long-term relationship later.


The dress that helped me land a second date with the man of my dreams.

I’m a straight, white female, of average height and with average looks. In today’s world of plastic surgery, Photoshopping, liposuction, breast augmentations, and perfectly polished social media feeds, it’s almost impossible to stand out and hold a guy’s attention in the world we live in today.

That is if you are under the impression that beauty is merely skin deep.

Millions have bought into the lie that appearance and sexual attraction are the two major factors when looking for a significant other. If you don’t feel that spark or there’s no initial attraction from the moment you meet them, then the short answer is that person isn’t the one for you.

Simple as that.

Or is it?

I won’t deny that yes, you need to be attracted to a person before you start dating or get into a relationship. However, I will say that how someone looks isn’t everything. A lot of times an intellectual mind or a vibrant personality can transform that person into the most attractive man or woman on the planet.

Go against the grain and look for that person who has outstanding character. Someone who can make you smile even when everything in your life is falling apart. Someone with who you can go from being silly on a Sunday afternoon to sharing a tender, romantic embrace to discussing current events in the world.

Looks won’t last more than a couple of decades but a personality lasts a lifetime.

This type of person is going to be harder to find, yes, but it will be worth it. Trust me.

(If you’re losing hope in your own journey, keep believing. It can be rough at times but it’s worth it.)

How to get a guy’s attention in the 21st century

The funny thing is that when you’re single, a guy is most likely not going to pay as much attention to you as you will be to them. You’ll be out there walking down the street, looking at every eligible guy who passes by, sizing them up, analyzing their looks or their style. But from the guy’s perspective? It’s highly likely he’s looking at his phone, talking to someone else, listening to music or staring off into space, thinking about whatever he’s going to do next.

You might have to send a few dozen selfies before you meet the right guy.

I can safely say from the other side of the spectrum that when you’re in a relationship, you will receive a lot of attention and looks from the opposite gender. Maybe it’s because people in happy, healthy relationships are…happy? I’ve been told that nowadays I seem to glow which naturally attracts people. And who wouldn’t want to be around a happy, positive person?

It wasn’t actually until I broke the habit of trying to envision a future with every guy I passed on the street that I freed my mind from a type of prison I didn’t even know it was stuck in.

I set myself up for disappointment and rejection literally hundreds of times. And it was all totally unnecessary, now that I look back on my single -and slightly desperate- years.

What you don’t want is attention from a guy who doesn’t fit well into your life or has drastically different standards than you do.

The best advice I can give you here is to not be so focused on finding the most attractive person out there but to make sure you don’t miss out on an incredible person who may be wrapped up in a nationality that you weren’t expecting.

Meeting in person vs meeting online

In 2018, there are so many ways you can meet someone. Distance is no longer an obstacle when it comes to staying in touch with them or showing them how you live your daily life. And the number of ways you can contact someone has increased to nearly a dozen (or more)!

If you’ve ever seen the movie, “He’s Just Not That Into You (2009) you may remember Drew Barrymore’s character saying,

“I had this guy leave me a voicemail at work so I called him at home and then he e-mailed me to my Blackberry and so I texted to his cell and then he e-mailed me to my home account and the whole thing just got out of control. And I miss the days when you had one phone number and one answering machine and that one answering machine has one cassette tape and that one cassette tape either had a message from a guy or it didn’t. And now you just have to go around checking all these different portals just to get rejected by seven different technologies. It’s exhausting.”

Quote from IMDB
Celebrities discussing dating and relationships
Dating relationships in movies and dating relationships in real life are not the same in the slightest a lot of times. (Photo taken from here)

The funny thing about that movie now is that almost all of those technologies aren’t even used to contact someone post-date. And that was only 9 years ago!

(I do feel slightly old saying that but oh, well.)

Instead of listing out all the ways you can contact someone now, I’m just going to say that while it’s perfectly okay to meet someone online (and then later on in person), you should ideally strive to spend the least amount of time getting to know them online.

If you’re an introvert like me, you may not mind texting or messaging a guy you like first before you meet them in person. This mostly described the way I would go about things the first year and a half I spent casually dating or meeting guys from different parts of Spain (and the UK). My friends, who were in real, long-term relationships told me that nothing can quite replicate the way you feel or interact with someone in person.

Communication is key in dating

Seeing them with your own eyes (and not by way of a webcam). Listening to their accent or the way their voice changes when they talk about their life or tell you about their favorite things. Watching their face morph into dozens of expressions instead of just settling for an emoji to tell you how they feel. Brushing your hand against theirs either accidentally or on purpose. Locking eyes with them or catching them stare at you with a dazed look in their eyes while you’re unaware.

All of these things are key things that you must experience with someone in person before you can really know for sure if you’d like to go on a second or third date. Or to help you decide whether or not you like them.

And though I had gone on several in-person dates about 2-3 years ago in Northwestern Spain, I let myself get caught up with guys who knew how to write the right things but I let months go by (and distance was an issue) before I ever met them in person.

I didn’t know what I was missing out on.

But, after having the experiences I had, I hope you will take the advice I should’ve taken at that time in my life:

If you meet someone online, try to move as quickly as you possibly can to meet them in person. Spend the least amount of time talking to them virtually and more time one on one.

Though I don’t highly recommend Tinder, I have used it and surprisingly met a good amount of interesting guys (even two PhD candidates) mostly in Santiago de Compostela in 2015-2016. I don’t recommend using it in the US for its reputation there, trust me.

The funny thing about life is that sometimes it will throw you a curveball or put someone in your path whom you never saw coming.

What I mean by that is how I met my now boyfriend (who, after a few days of publishing this put a ring on it). We met in person through a mutual friend at a local café in the city where we both lived. For anyone that loves a sweet, wholesome story, the first time we ever met was at the Bible study he was asked to lead by said mutual friend. I wasn’t interested in native English speakers (let alone ones who spoke differently than I did) at the time so I first got to know him as a friend. I thought he was really cool but he soon moved away from Santiago de Compostela and I didn’t know if I would see him again but I became friends with him on Facebook to stay in touch.

It all started with a cup of tea…and the rest is (a rather long) history. [Lusco y Fusco Café/Bakery in Santiago makes amazing tea and baked goods by the way!]

And now three years later -and a wee bit more than one year together-, we are very much in love and live in the same city again but this time la capital – Madrid!

It’s funny how life can change so quickly in just a few short years.

But remember that the time will pass no matter if you say “yes” to a date with this guy or that other guy. So do yourself a favor and disconnect from this technology-obsessed culture and have a cup of coffee (or tea) with someone, face to face.

You’ll thank yourself later. 😉

Should a girl ever ask a guy out, even for an “informal date” (coffee, a walking tour, a drink, etc)?

Unlike the teachers at my Christian high school and most of my American Christian friends, I don’t think there’s anything wrong with men and women being friends. I grew up with an older brother and had lots of friends who were guys. I was friends with a few girls my age (and later made friends with more girls in college) but they were few and far between.

The main thing you need to keep in mind here is to set boundaries. Don’t open yourself up right away to every guy you meet, even if he seems like the nicest and kindest guy in the world. Just like you would with friends, don’t spill out your whole life story to someone you’ve just met. Let the stories and experiences come out naturally and organically. Let it run its course and don’t feel like you need to rush to tell them your deeply personal stories about your life.

Tea and latte dates with friends
A cup of tea is really the best way to start to get to know someone.

On the contrary, if you live abroad, it’s highly likely you’ll move past the more superficial ‘getting to know you’ questions with someone a lot quicker. The depth of your conversations could be escalated due to a number of different factors: you’re both from the same country, you both actually speak the same language, you both went to the same college but different years, you both lived somewhere else in the world and loved it. The list of possible similarities could be up to a mile or two long!

Regardless of what commonality draws you and another person together, you also can’t forget to factor in culture. The culture and subculture you grew up in will affect you for the rest of your life. And where you currently live will affect how you interact with people daily and live your life. While you may have been able to wait for a guy to ask for your number or ask your friend to ask one of his friends if he likes you (side note: don’t ever do this, it’s juvenile) back home, you may not be able to do those things where you live now.

Find someone who will send you a greeting card just because. Those people are the best! 🙂

Let me give you some examples.

In Spain, men aren’t as proactive as American or British guys are. I’ve gone out with Spanish guys and while most of them were very nice and we held good conversations -or even met up another time-, they tended to be very passive when it came to taking the initiative to make plans or ask me personal questions in person. I had one guy text me after we had a drink and a tapa if I liked him. I ended up saying no -and still would’ve said no because our lifestyles were actually quite different- but I would’ve liked it if he had asked me that question in person.

One of the major things that turned me off from dating a Spanish guy was the lack of initiative and passivity towards relationships. Maybe I’ve only met shy, more introverted Spanish guys? I don’t know… I did learn from those dates that, while I’m a very headstrong and independent woman, I want a man to ask me out. I want to see that he will follow through on his word.

But in my relationship now, sometimes I plan or give a suggestion as to what we do on a date for that given day or weekend. It’s not called compromise, in this case, it’s called teamwork.

ice cream dates
Helado, xeado, gelato, ice cream…whatever word you use for it, this can be a simple yet fun date, too!

In North America, where I’m from, guys tend to put pressure on girls to be more physical with them early on in the dating phase. There are some British guys who are like this as well -I’ve met at least one- but it depends on what part of the British Isles they’re from. Even other regions of England are quite different from one another! (Things you don’t learn about at school in the US, haha).

In my experiences with crushing on American guys-I’ve never dated one-, I found a lot of them to be focused on staying in one place. Graduating from college, getting a good job, moving up in the company or relocating to a new department and then….just living their life in the same place. I’ve met a few in different European countries who like to travel but most never really seem to want to stay living abroad. Or in Florida, I found that the guys I liked preferred to stay in Florida. The fact that I was from a different state (and the North) seemed to be an unspoken deal breaker. My mom has always told me, “the best things are the farthest away,” so I could never understand why distance could be a deal-breaker for someone.

That is until I met three British guys who would all alter the course of my life to some degree or another. Looking back on those meetings,  I realize that I met them in three distinct years and at three distinct points in my life. And at three different ages, too. British (read: English) men are a lot more formal when you first meet them. They also don’t share intimate details of their lives with just anyone. You have to get to know them quite well before they will. And it may take several dates and endless amounts of chatting later to really move into the title of “close friend” or “girlfriend” for that matter. If you’re willing to invest the time into getting to know them and the feeling is mutual, it will be worth it.

What’s my point after all those twists and turns we just took navigating through other cultures?

Well, the answer to the question I asked earlier is that it depends on you. I have asked guys out before and it hasn’t always gone well. But, over the years, I found that while I don’t see a problem with a girl asking a guy out, I prefer a man takes more initiative with me. I was let down immensely by someone else a couple of years ago and got emotionally invested in him way too soon and that taught me a big lesson. If a man liked me and wanted to date me, I needed to see that he was not only serious but that he would keep his word. That he wouldn’t let distance or time or work stop him from seeing me.

Churros con chocolate date
And if you’re a bit shy, you can go on a date with another couple. Having other people around might lighten the mood for you. 🙂

It was a hard lesson to learn at the time but if you learn to wait for this type of man, you’ll save yourself a lot of inner turmoil and heartache.

Learning to be patient with communication 

Why you shouldn't be dating any other type

It literally took me years to develop the patience I have now when it comes to waiting for a response from someone (even just from family members or friends), especially text messages. Don’t start thinking I’m an expert on patience because I haven’t had a huge amount of it for more than two years now. And it took a couple of decades to get to that point.

Here’s an example of my thought patterns not too long after I started dating regularly when a guy I liked didn’t reply back quickly (read: in 5 minutes or less):

Message sent.

A few seconds later…

Thought #1:

“I’m sure he’ll like the funny way I explained (whatever you said), he’s surely bound to reply back pretty soon now.”

A minute or two goes by…

Thought #2:

“Or maybe I was *too* funny or not funny enough?”

Another minute later.

Thought #3:

“Or what if his phone is on low battery, meaning he can’t check his WhatsApp messages yet?”

A couple more minutes go by…

Thought #4

“Wait…is he avoiding me? Or ignoring my messages but clicking on someone else’s while he’s online?I see him online right now. Could he be interested in someone else?”

Here’s what I would say to myself back then if I could:

No, Sarah. If a guy is ignoring you, he’ll take a week to respond to your message and then make it seem like he was so overwhelmed and preoccupied that you should feel sorry for him. So if it’s been 5 mins or heaven forbid, 10 minutes, and he hasn’t replied, just chill.

Go do something else.

Get on with the rest of your day.

(Unfortunately, this advice is based on a personal experience I had a couple of years ago).

The most important thing I’ve learned about communication is to be patient and let people respond to you, in their own way and in their own time.

Bustling Plaza Mayor in Salamanca at Night
Just like in the Plaza Mayor de Salamanca (or any square in the world), everyone’s got places to go and people to see. That’s life.

Now, whenever someone takes more time than I would like to respond to me, I remind myself that people have their own lives.

A guy or anyone else who’s taking his time to respond to you is living their own life. Working, commuting, driving, exercising, sleeping, etc. Heck, the guy you like could be calling his parents or grandma for a weekly check-in for all you know.

Just chill. The right (and mature) person will write you back and won’t ignore you. He’ll make time for you and make you a priority in his life. He’ll even spend (and maybe even enjoy spending) money on you or money to see you if you don’t live in the same city.

And if the person you’re currently interested in can’t (or won’t) do that, move on. Don’t settle for someone who only has you around as an option and hasn’t either committed to getting to know you better or committed to being in a monogamous relationship with you.

Because you’re worth it.

Date the girl who reads
Focus on being the person you were created to be. If this photo describes you, great. If not, be that girl. Just don’t ever pretend to be someone you’re not.

Changing yourself to be who they want you to be or dressing up for a man

The above photo leads right into what my remaining thoughts on this are.

Don’t try to change your personality or physical appearance into something that’s not naturally you. If someone isn’t completely head-over-heels for who you are, then they’re not for you.

Remember earlier in the post when I mentioned the dress I wore that landed me a second date with the man of my dreams?

Well, I didn’t necessarily wear it because the guy I was going out on a date with loves the color blue. And I didn’t buy a new dress just for him.

I found it in a cute shop while I had a short layover in Sevilla after my train arrived (and before I caught a bus to where he lived) and I knew I would feel amazing in it. I also didn’t have a dress packed in my bag…so I had to find something. Luckily Spain is full of inexpensive clothing stores (and I wasn’t shopping in Madrid) which reassured me that I would find something before that Friday night.

Advertisements who like someone you used to date
An ad that would later haunt me for most of my first year in Madrid because I was trying to forget a similar looking guy I shouldn’t have been trying to impress or change myself for in the first place.

The difference between that experience and another first date weekend I had was this:

I didn’t need to buy the dress in order to make that guy like me.

He already did and I liked him back.

I bought that blue dress in 2017 because I wanted to put my best foot forward if/when our date weekend turned into something more serious.

So, my advice for you, if you’re a young, inexperienced woman who wants to date and meet guys is to always be the best version of yourself.

Keep these things in mind when going on a date with a guy:

  • Arrive on time
  • Maintain good hygiene and dress sharply
  • Be attentive towards the other person (if it’s getting late or if they need to drive a long way in bad weather, let them leave)
  • Relax, keep a good conversation going – and enjoy yourself!

Dating and being in a relationship mean sacrifice

There’s no other way to describe this section other than to be blunt.

Relationships aren’t easy but the amount of effort you have to exert may not seem like such a task once you’ve found the right person. How can you tell? It will come naturally to you.

After all the dozens (or hundreds) of times telling your life’s narrative, what you’re looking for in a mate, your hobbies, what languages you speak, places you want to visit, dates and outings, splitting the check or not splitting the check, deciding whether or not to kiss their cheek or their lips, writing hundreds upon thousands of texts, waiting for phone calls/messages/FaceTimes, it’s a worthwhile sacrifice if the person you’re pursuing is pursuing you at the same time and at the same speed.

flowers on a Valentine's weekend date
Even if it means you have to wait until you’re 29 to receive your first bouquet of flowers.

Above all, I would urge you to not look for someone who gives you the most excitement or the most thrill but to look for someone who gives you the most peace. Someone who helps you. Someone who calms your fears and worries and most of all, someone who pours gasoline on the passions in your life and sets them ablaze.

If the person you like or the person you’re dating right now, only brings more trouble into your life and you constantly have to beg them to remember to do things…cut them out of your life.

If I’ve learned anything in the eleven years I’ve spent living away from home it’s this: don’t keep someone around if all you are to them is an option.

A guy who is committed to and devoted to having a healthy relationship with you will have you as his highest priority and he will still be able to find a way to balance everything else in his life.

The verdict: is it worth it?

Find your forever taco date
It definitely is once you find the person who looks at you the way you look at tacos or insert your favorite food here.

Is there anything I missed? Anything you’d like to add? Join the discussion below. I’d love to hear about your experiences of dating someone from your own country or a foreign one.

Stay tuned for part two of the Confessions of a Late 20-Something series next month!

Leave a reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.


Verified by MonsterInsights