Another day another guide for you. This time it has nothing to do with restaurant recommendations or coffee choices but rather what it’s like dating in a big city, dating in general, do I date?, what I care most about when dating, stigmas to break up with and more. I’ve thought about this for quite some time now and for the past three years that I’ve been dating, whether I like to admit it or not, it’s been a pretty big part of my life. I feel like some people say it’s a whole entire extra full-time job and in 2019, that couldn’t be more accurate.
Coming from someone who used to work at a predominately female company, doesn’t drink alcohol and hangs out with mostly wellness bloggers who do yoga (I’m laughing at how this all sounds), I don’t surround myself with a ton of guys. Therefore I don’t have many opportunities to meet guys through work or friends. Not a lot of options to meet “the one” or anyone that’s a male in general. To top it off, I went to an all girls high school (truly not as bad as some of you will think) and a Jesuit private city college that was 70% girls. The majority of straight guys at my college were either in frats that definitely didn’t have the same interests as me or were not my type whatsoever. Or better yet, they had a girlfriend.
As you can imagine, it was pretty much close to impossible to date in college. When I was a freshman in 2013, the only dating app that existed at the time was Tinder but then it was such taboo. You only went on it if you wanted to “hookup” and if you told people you were using it, you felt kind of shameful in a sense. I think I maybe went on it once as a joke with my friends right before our Freshman year of college (2013) and never in my life thought I’d meet a guy from an app.
I went on my first real date with a guy from Tinder – in fall of 2014 with a friend of a friend, who happened to go to my college. At the time I didn’t think much of it because we ended up meeting unexpectedly at a concert before our “first date” and I didn’t count it as a real Tinder date since I somewhat knew of him beforehand. I then went the rest of my sophomore and junior year without talking to/dating a single guy, until I met someone in 2016. This guy proved to be what I needed in the right place at the right time, especially as I dealt with my mom being sick all of 2016/beginning of 2017. I look back and think of how much of an impact this guy had on my life as he literally was in the background of it for 3 years. After just 8 months of knowing him, he not only cheated on his ex-girlfriend but then me and then continued to talk to me while he had a new girlfriend of a year and half. I like to think that he taught me so many lessons. The lesson of knowing we as women deserve to know the difference between what we think we want and what we deserve, knowing not to settle and most importantly, how we should be respected and only date people who actually want to be with us and no one else.
Those who care about us, our interests and don’t mind if we’re sober or not, if we eat healthier or if we don’t workout at all, if we look a certain way, if we’re wearing a spirit jersey and leggings or a leather jacket and jeans. In the past three years, I’ve found what matters most is those “non-appearance compliments”, the way you really can connect with someone and when you know they only want to focus on you. If you can actually talk to a person and look them in the eyes without looking away – try it… I’ve found this how you really can feel a connection. It’s a thing. When you date someone, they like and enjoy you for you. And if they don’t and can’t – they’re not the one for you. It’s really as simple as that and I find we’re constantly complicating things for ourselves, and for one another.
This guy made me realize that at the end of the day, the only person I needed was myself. I learned that it’s so easy for someone to get inside of your head and heart. To let you think you’re “in like” or in love with them when in reality it’s just an idea of them that you want in your head. That it may be hard to lose them but in reality, sticking with them and having them hurt you for longer is even worse. And at the same time, they’re hurting other people in your life the longer you let them stay in yours.
For the two years (2017/2018) after I stopped talking to this guy, I would compare everyone to him. I think this is something we often fall into when we date someone who mistreats us. We compare and compare. We compare ourselves to others and we compare others to our past relationships. Thinking it’s always us and we’re never good enough to find someone new or to move on.
I think it wasn’t until this year when I really moved on from this person. I think the combination of cutting him out of my life and leaving my corporate job was like my life did a whole 180º. My one friend, Christina, in particular would tell me time and time again that it wasn’t until I cut him out of my life completely would I find someone else or happiness/positive energy outside of that toxicity.
When I brought up the topic of dating on Instagram last week and had people ask me questions, someone asked me why I usually never talk about dating. The answer: I personally think that dating for the most part is the one thing when it comes to social media that doesn’t need to be publicized. It’s such a private matter and because I’ve never had an “official boyfriend”, I don’t feel the need to post about the random guys I talk to here and there. Can you imagine me posting a photo of a guy on Instagram stories and then the following week we’re not talking? Awkward… Also I could only imagine the amount of messages I’d receive.
Back in January, I went to one of the La Colombe’s I often visit to get my usual black and tan (favorite coffee drink) and instantly felt this energy towards my barista. I was so attracted to him, knew I had seen him before somewhere and had to say something. This was my point when I thought to myself, why are we all so scared to meet people out in the real world? Or “out in the wild” as some people say. If not now then when? If we keep telling ourselves nothing will happen, nothing WILL happen.
While I didn’t ever end up going on a date with him, I did find the courage to give my number to his co-worker to in return give to my “barista crush”. I felt empowered for trying to make a move and make a statement for once, outside of social media and outside of dating apps. I thought after that situation that I’d continue to go on dates from that point forward of course but try to push myself to talk to more strangers, meet new people and step outside of my comfort zones. Because once you stop forcing specific things to happen, that’s when they really will.
I have tons of friends and old co-workers that have met their current boyfriend/girlfriend from an app, and even had a co-worker last summer who married her Tinder match. It’s incredible how apps can really connect people. I partnered with Hinge on social content earlier this year and I have to say out of all of the apps, they are my favorite. The app gives you prompted questions to answer so that you can kind of get a sense for who it is you’re going on a date with, if they drink/smoke/are religious, etc. It’s extremely descriptive and goes just beyond how attractive a person is. I also feel like if a guy comments on one of your questions or photos as opposed to just liking your photo, they’re probably a more decent human.
I used to think that when I went on dates, it was in hopes of finding my next boyfriend. That I’d go on a date and I’d fall madly in love with whoever I met and that would be the end of me dating in my 20s. Then I realized, that’s not realistic and I need to think of each date more so as “what will I learn from this person?” and treat it just like meeting any friend for coffee/a drink. Most of the time (hopefully) you’ll have a good conversation, experience a new restaurant/bar in the city and be social in a world that sometimes seems far from it when we’re always on our phones. In the past few months of dating I’ve tried to think of it as a learning experience and a positive thing that I get to meet new people (even if for 30 minutes and never again). I try not to take anything too seriously and I almost never get nervous for dates anymore because truly it’s a waste of energy.
I also try my best not to get discouraged when dates go wrong or when I like someone and we stop talking. A huge tip I have for not letting this get you down is thinking that you’re lucky that person didn’t work out and in the end, they were just a stepping stone to someone better for you.
Last year around August, I ended things with someone who meant a lot to me and I remember I had never been so sad in the longest time. I cried that night, the following day, left work multiple times to cry – it was one of the weakest points I felt and looking back on it I think, why though? The following two weeks, I had to focus on myself (due to my surgery) and then right after that, I decided I was done being sad and feeling sorry for myself when in reality I could turn the bad situation good and make something for myself. I started meal prepping consistently, working out with my trainer 2x a week, noticing a difference in my physical and mental health and excelling at my job. All things that truly got me away from the negative thoughts of not having someone around me anymore.
It wasn’t until that relationship ended that I truly realized I could be so content and happy on my own, I just needed those specific situations to happen in order to get there.
I’m happy to share that at this point in my life I’m just going with the flow of things but truly focusing on myself first and foremost because at the end of every day, you’re always left with you. It really is true you can’t let someone else appreciate or love you until you love and care for yourself. When you put your mind, body and health first, then you can focus on someone else’s and have them learn to appreciate those things about you.
Now since I was asked a ton of good questions on Instagram about dating I’m going to address your guys’ FAQ’s below. Let me know your thoughts, if you have ’em.
How do you get over the fear of dating? I’m terrified.
I try to remember that the second (literally) I see them, I’m no longer nervous. Maybe it’s just me but when I get nervous I try to think of this because it always works. I also realize how it’s not the end of the world, it’s JUST one date, you’re usually always in a public place so you’re safe and at the end of the day, you’re just having a conversation talking about life/yourself/fun things in theory. I like to think of the person I’m meeting as an Instagram friend (because I have so many from Instagram that are bloggers) so that’s the easiest for me. At the end of the day remind yourself, you are you and if they don’t like you, they’re not the one for you but you were yourself, met someone new and went out of your comfort zone. So even making an effort shows your power.
Favorite safe spots in Chicago (drinks/dinner/activities)?
The best part about being in the city is there are truly so so many options. I always think there’s nothing to do if you don’t drink like me but that’s far from the truth. I love going to a coffee shop (Colectivo, La Colombe, Dollop, Café Integral, going for a walk in Lincoln Park or Wicker Park, getting sushi (Sushi Dokku is my favorite), drinks at Broken Shaker, The Berkshire Room, The Violet Hour (super intimate), Young American (they have CBD cocktails/mocktails) or dinner at Lula Café (the first time I went here was a date last summer and it was the best gnocchi I ever had), True Food Kitchen (casual but sit down), or get tacos in the summer at Big Star or Antique Taco (such fun energy, vibes and good food). I’d say especially if it’s the summer though, just get coffee and go for a walk and talk. Nothing better.
How do you tell someone you’re not interested – politely, of course?
I have been on dates with guys who text me after interested in hanging out again and while I used to “ghost” some people, I realized that do I enjoy when people “ghost” me? Obviously not. So now I’ll say politely over text, you know I don’t think this is going to work but you’re a great person. Spreading that good karma.
How do you open up to someone about your anxiety/grief?
I would say I wouldn’t open to someone about this or more serious things until 3 dates in. I mean honestly it all really depends. Are your first two dates only an hour long or is your second date 12 hours long and you stay up until 5am talking to one another? You know? It all depends. I’ve really only opened up to two to four people that I’ve dated about my experience with grief and anxiety. I think you really know when someone cares and wants to hear about you vs. someone who literally just wants to hookup with you. Of course I really want them to know who I am as a person and I’m already vulnerable online/my blog but I hate when people “feel sorry” for me in a sense. I really appreciate when a guy just takes in the information, is understanding and overall just knows that information I’m giving them feeds into who I am as a person.
Advice for someone dating after heartbreak?
I’ve experienced heartbreak twice and I think both times the hardest part when dating again is not comparing whoever you’re on a date with to the person you loved prior. The best advice is instead of comparing, learn to appreciate the new date for who they are and realize no one is the same, and that’s okay. Honestly that’s why dating is so fun. I also think if you go on one date after you’ve had your heart broken and don’t feel right, just don’t date for a while. It’s that simple. No one is forcing you to do anything. You’ll know mentally when you’re ready to move on from your heartbreak but until then, just focus on yourself. There’s nothing wrong with being alone and wanting space for yourself and your own healing.
How do you balance sharing big things with someone on a first date/not overshare?
I personally love love love random questions and asking guys questions because I am fascinated learning things about someone new and in return I hope they’ll think the same towards me. I remember this one date I went on a guy said, “you ask a lot of questions” as he literally asked none. I’m sorry but how are you supposed to engage in conversation and get to know someone else if you don’t ask questions?! Like duh… But I think the key to not oversharing is knowing how the first conversation goes.
Start with small talk (sadly we have to do it in order to get a sense of who the other person is) but then just ask random questions. Once you ask the random, over-the-surface-level kind of questions you can definitely can get a sense of who they are and what you feel like you should share. But I definitely don’t pour my heart out on a first date when I know the date most likely won’t go anywhere. No sense in telling my life story to a guy who I won’t see again. It’s kind of like giving your life story to your flight attendant. It’s a waste of energy for both people.
What is your opening line on apps/when you meet someone?
If I’m on an app I like to say “tell me something interesting about yourself” because I mean, they have to then, haha. If I meet someone in real life I feel like I usually start talking about music because I love connecting with people over that… or you have to go off of something in the moment. Ask them what their favorite taco is or if they believe in witches, magic, spirits. Like truly, who cares.
When do you end up telling someone you’re a blogger?
I used to say it into the first date. Sometimes I’d say it texting prior to the first date because I hate hate hate when guys make a big deal out of it or talk to me like I’m on an interview about my blog but then again, everything my blog focuses on is what I do for a living and my hobbies. I focus on lifestyle content, my favorite restaurants, yoga, etc. That is essentially, my life. So it just makes sense to share that right away. I just hate when I send a guy my Instagram and they say “wow you’re famous” because I never like that kind of attention and I also never care about the size of my following. Also.. I’m not famous! It’s hard but it is what it is.
How do you go out on dates if you don’t drink – how do you tell them that?
I used to think this was a huge issue but then realized, if a guy will judge me for not drinking… how will I date them? We most definitely aren’t meant to be together. How will we even get along if all they do is drink and that’s the opposite of my lifestyle? Right? I choose not to drink for personal reasons and really only do maybe 3-10 times a year. I personally hate the way I feel when I drink (even if it’s 2 cocktails) and only like the taste of gin and vodka (truly I don’t like wine or beer). Every now and then I want a drink but it’s rare. I always suggest coffee, lunch or dinner for a first date over drinks but if I do meet a guy at a bar, I just order club soda. I’ve done it twice now and I always get nervous more so of just ordering club soda than I do of meeting them (ridiculous I know haha) but then in the end, I feel better overall and it’s fine. It’s only a big deal when you make it one.
What is your biggest turn off?
Many things. When a guy talks to you in a condescending tone, when they are on their phone texting in front of you, when they don’t ask you ANY questions and only talk about themselves (hello ego), when they have a girlfriend while they’re talking to you (obviously that’s a turn off) and disrespecting me/judging me for my lifestyle and/or job. Thank u, next.
Why do you think guys are so intimidated to come up to talk to girls?
I think they’re predominantly scared and nervous, just like girls are to come up to guys. A huge part in why I don’t go up to guys in coffee shops or on the street is 9x out of 10 they will have a girlfriend. Apps and social media have pretty much ruined our ability for the most part to meet someone “in the wild”, too. This is why so many people only think they can meet people socially with the help of alcohol or bars which is one of the reasons why I love not drinking is because it pushes you past relying on that.
Best date story?
I mentioned this on Instagram stories but I’ll share it again here. This was a second date with a guy but we got sushi and then he drove me to south Lakeshore Drive past Soldier Field as the sun was setting and I could see the skyline from the southside which I had never seen before. So pretty much sushi and a walk accompanied by a 4-6 hour talk after. I think those are the best dates really. The simple ones where you can end up talking for over 4 hours. I always know that’s the sign of a good date, as opposed to talking for 15 minutes. I once had a date that (I shit you not) from my front door, to the coffee shop and our walk back to my apartment door was 40 minutes. Maybe fastest date ever and ask me if I saw him again… I think you know the answer.
I hope this gave you guys a glimpse into my views on dating, how I date, what my thoughts are, etc etc. I know it’s probably one of the most annoying things to do is dating in your 20s/30s but at the same time, think of all of the incredible people you meet and learn from along the way. I always try to think of the positives that outweigh the negatives (like when someone gets mad you ask them a question – you good, sir?).
Photos by Samantha Parquette