The 13 Most Annoying Things When Dating As a Millennial

This is a post I’ve been wanting to write for a while because, well, I’m in full force dating as a millennial. And, while it can be fun and definitely a thrill, it is so annoying. Let’s be honest, there are so many good-looking guys out there. But there are also so many good looking girls out there, too. And that’s nerve-wracking. Because of social media, we’ve caught ourselves comparing little things that once didn’t matter. But as much as we try to get out of it, we just can’t. We’re social media obsessed. We spend hours on dating apps, Facebook, Instagram… we see photos of beautiful girls going out and wonder why we should even bother dressing up to go to that one bar on a Friday night. But that’s the issue. We no longer go out to have fun with our girlfriends. We go out to find someone. To feel better about ourselves. Why can’t we feel better about ourselves on our own?

Now, I’m guilty of all of these things. I spend hours on dating apps, thinking of clever messages to send, and stalking social media. So that’s why I thought it would be fun to change things up on The Fashionista’s Diary today and share with you the annoying things I’ve found while dating as a millennial. Do you agree with any of these? Are there any that I missed? I would love to know in the comments below!


I can’t even begin to tell you how many times I’ve sat down with friends and we’ve relayed different scenarios in our heads based on her response to one simple text message. He said “ok” so do I respond? Does he really mean “lol” or does he want me to stop texting him? He asked me what I’m looking for, do I tell him the truth or just say a hook up? We focus so much on saying the right things that we actually lose our honesty in the process. I’ve “ruined” a lot of conversations by saying how I feel. And, to be honest, I don’t plan on ever sending a false response in hopes of making a guy like me. At the end of the day, he needs to like me for my silly and honest responses. If he doesn’t then tell him boy bye.

Oh my gosh. This is irritating. Like I said up above, not only do we worry about what we are going to respond, but we also have to try to figure out what he’s trying to say. I remember one time I was sitting with a friend and a guy told her his weekend plans. She took at least 2 hours to try to figure out what this meant. I really thought it just meant that he was going to sit on his couch on a Friday night and watch TV – NOT. We both thought that it was an invitation for a hookup. So, she responded accordingly. Well, things got awkward really fast when we found out that those really were his plans. Did they ever end up hanging out? Nope. Sometimes texts really mean what they say. But because millennials texts guys/girls they have yet to meet, they don’t understand the meaning behind a lot of texts. For example, I’m a really sarcastic person. I like to joke around and have fun with conversations. Some people take my sarcasm as me being mad and it has even turned into full blown fights. This is why you pick up the phone and call, people! It’s so easy to get caught up in miscommunication and it’s honestly not worth the hassle.

True story: I once hung out with a guy and we had a really great time. We had lunch then went to a rooftop bar and got drinks. So, of course I assumed we would hang out again soon. Wrong. He told me I needed to pump the breaks and wait a few weeks for our next date. I’m sorry, what? As a millennial, it’s not cool to hang out with the girl/guy you’re talking to all of the time. And I honestly find this so annoying. If you like someone and enjoyed their company, set up a second date. There’s no need to play hard to get or wait weeks to see them again. There are plenty of fish in the sea. It’s just as easy to catch another one as it was to catch you. Just sayin’. There’s never a clear answer. Are you dating? Are you talking? Are you hooking up? Are you just friends? Is it too soon? No one ever knows and you just end up being in the weirdest limbo wondering if you should be keeping your eye out for other options or putting all of your eggs in a basket that might not even exist. And don’t even bother asking him what you are. That’s moving too fast. [Source]
My friends make fun of me because I’m on basically every dating app that exists. I have no shame in it. I think they’re fun and sometimes I’ve gotten some great dates out of them! But, I’ve become so obsessed with swiping while walking home, on the subway, while watching The Bachelor, etc. that I’m no longer living in the moment and enjoying my time with my friends and family. Do I have a new match? Did he answer me? Why did he unmatch me? It becomes a vicious cycle of bouncing from app to app trying to find the candidate of the week. We no longer meet people organically because we have our noses in our phones while we swipe away (mind you, I’m saying this as I just got a new match on Bumble). First dates are no longer cute coffee dates or lunch dates. Instead, they’ve become late night drinks where the guy tries to take you home after. Um, no. I don’t mind drinks… but at least put some food in my system first and not just some cheap-tasting alcohol![Source]
Because of all of these dating apps, we swipe solely based on looks. Sure, we’ll look at their bio. But even if they say the sweetest thing, if they’re not cute, we say no. As I’ve grown up, I’ve realized that if a guy is really sweet and not that good looking, he becomes so good looking in my eyes because of his amazing personality. But when you’re on a dating app it’s hard not to judge solely on his looks. It’s the sad truth. Oh, the joys of social media. Even with blogging, it’s so hard not to get caught up in comparing yourself to every other blogger. Now, imagine you’re trying to date and feel good about yourself and you see these gorgeous girls with amazing bodies. Not the best feeling. Social media is a constant reminder that there are so many other good looking people out there, people prettier than you, and it sucks. But as millennials we’ve grown up with social media for years and it’s hard to change our habits of scrolling through our feeds late at night before bed or early in the morning before work. We’ve become accustomed to constantly comparing ourselves and not feeling “good enough” for the guys that are out there.

[Source]I heard this term for the first time this summer and I thought it was funny. Well, now I don’t think it’s funny. This is probably one of the most annoying things ever. If you don’t like someone or no longer feel it, let them know. I remember I had matched with a guy and we were supposed to get coffee on a Monday. Well, he disappeared and I had no idea why. Fast forward a few days and I see on social media he has a new girlfriend. Well, don’t you think it would have been easier if he was just straightforward with me? I think yes. But ghosting is an easy way out. And, thanks to the fact that we mostly text each other instead of actually hanging out in person, it has become extremely easy to do.
If you tried filling up a football stadium with the amount of people on Bumble, The League, Tinder, Hinge, etc., you’d realize there are too many of them to even fit in a huge stadium. We have way too many options. Yes, there have always been millions of people in this world. But because we have these apps, we can happily swipe no to one guy because we know there will be a better one showing up on our screen really soon.
If I go to a bar, I never go up to a guy and ask how tall he is. If I’m wearing heels and he’s taller than me, then I’m happy. This isn’t the case on dating apps. Instead, I’ve become so obsessed with the idea that a guy needs to be 5’10 or above. My friends laugh at me because I’m only 5’3 and it’s a ridiculous expectation to have. But… blame it on the apps. So many apps actually show a guy’s height, so of course I set my lowest height at 5’10. Because of these apps, the smallest things can become deal breakers. Things that we wouldn’t notice in person are staring right at us.  [Source]
I remember one time this guy and I had been talking for almost a month. He posted a photo on his Instagram that I really liked so I commented with the heart eye emoji. Within 20 minutes, my comment was deleted. I asked him why and he said it was because he didn’t want people to see it and then if something were to go wrong between us he would be embarrassed. Haha… ok. What does that even mean? I didn’t know that commenting on someone’s photo automatically meant that we were officially dating and the whole world knew it. Little things like this are crazy. My friends and I talk about it all of the time. We never know when or if it’s okay to comment on a guy’s social media. I don’t even understand why it should be a problem. If a guy likes me and comments on my photo because he likes it, I would be thrilled! But this plays into the idea of acting “chill,” which I’m not really an expert on, apparently. Haha – this one makes me laugh so much because I possess the least “chill” personality in the millennial dating scene. When I want to text someone, I’ll text him. I don’t wait for him to play his wait-24 hours-game. If I want to see a guy, I tell him. But every time I get the response “chill” or “wow moving fast, huh?” I want to throw my phone at the wall (I don’t do this because I clearly need my phone for all the dating apps). At least as girls, we’ve become pros at mastering the act of being chill. When, in fact, we are in at least 2 different group chats with different groups of friends sending screenshots of the texts trying to figure out how exactly we can respond that will make us seem calm, cool and collected.

Lauren Ashley
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  1. Lacey- The Glitter Gospel

    This is hilarious! While I’ve been married for 3 years (almost) I still see this! The funniest thing to me is being a blogger and having randos popping up in the DM’s all the time. Like what? No thanks! You are a beautiful girl and the right guy at the right time will come along. I also think it’s a city thing. When I lived in Philly it seemed like all my friends were older than me (25-30’ish) and none of them had marriage on the brain, but my friends back in TN were either already married and then planning a family or getting married in the near future. Just live your life and let it happen!

    PS: if anyone ghosts you… they’re ignorant and it’s their loss!

  2. Ashley

    This is such a fun, insightful post!! You know I love following your dating life and living vicariously through you!!

  3. Stephanie

    Hahaha, girl you had me cracking up at these points! While I’ve been in a wonderful, steady relationship for over a year now, I see my friends struggling with these problems constantly and it makes me grateful that I kinda got out of the “dating game” before it became so complicated haha!

    Stephanie //

  4. Kasey

    This post is awesome! It’s funny because everyone gets really suspicious when I tell them my boyfriend and I met in a bar- which is true, but still we went through most of these! Communication via text, social media, labels, all of it!

  5. Jenn

    I’m 45, so not close to being a millennial, but since I’m newly single and on Match I can relate to all of these points! Let’s just say men don’t mature that much from their 20’s to their 40’s! I too am 5’3 and won’t even go out on a date with a guy if he’s under 5’10, I never cared about this in my 20’s, my tastes have changed over the years, so I’m glad I’m not the only one that’s a little obsessive over this. I will say you do have it easier as a millennial, you’re most likely not dealing with someone else’s kids and ex wife. I truly believe timing is everything.

  6. Irina

    I’m a little bit older than you but a couple of years ago I was talking to this guy on and off and he added me on Instagram. he posted a picture and I either commented with an emoji or wrote something and he deleted it. Later when he texted me I confronted him about it and he said he didn’t want anyone to think I was his girlfriend (so he could continue hooking up with other girls). So that was the end of that.

  7. Fallon Britney

    Thank you for this girl!!! You got everything right on the mark!!! I have been dating my guy for a few months now and I let it slip that I bought him a Valentines Day present. Just that I’m excited to have him get it. Beer of the month and candy Legos (a serious millennial lol). He actually have this four hour make me feel like crap text rant about how he’s complicated… YOU’RE NOT COMPLICATED PUMPKIN. YOU’RE JUST A MILLENNIAL!

    So thank you again. I needed this smile and laugh after my night lol.

    Fallon B.


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