What I learned from going on 30 dates in 30 consecutive days.

30tinderdatesin30nights Wide

A fancy infographic to review what I accomplished in 30 days.

30 Tinder Dates in 30 Nights

“I think it’s a great idea,” said my mom when I told her my plan to go on 30 dates in 30 nights. “Really?” I replied. It wasn’t the reaction I expected from her. My friends and the rest of my family were very supportive about it also. Except my grandmother, she was very worried I might meet the wrong kind of man. Ohhh grandma… don’t you know that’s what I’ve been doing for the past 15 years???

As some of you might recall, the idea for this challenge came to me on a random Sunday morning, after I realized I needed to get out of my comfort zone. I didn’t go into it thinking I would find anyone special, I went into it mostly to see if I could do it and to see if I could learn to be better at dating. Selfishly, perhaps, I thought it would make me stronger, smarter, less likely to get hurt. But I’m sad to report that the past 30 days didn’t make me stronger or smarter about dating. I did learn many things about people, and the topic of dating, throughout my diverse discussions with the 24 guys I went out with. But I am not any less vulnerable, nor do I have thicker skin than when I started. I did however, meet someone I actually like, and have realized nothing brings up my deep rooted insecurities like dating!

I thought long and hard about sharing my insecurities with the world because it’s obviously not the best side of me. But the whole message behind my blog is that it’s okay to be vulnerable, it’s okay to be insecure sometimes. Because the only way to learn to become a better person is by being honest about who you really are. That’s step one… then you have to face your toughest critic, which is yourself, and so throughout this challenge I’ve come face to face with myself and confronted my doubts and insecurities. Now if I could only wave a wand and make them all disappear! I made a list of my top five, because that’s all we have time for. This is where I come clean…

# 1 – I’m always myself, and sometimes that’s too much

Two days before my challenge was complete, I wrote this sentence: “I feel guilty and also unsure about how to continue this challenge, I’m starting to like someone and I don’t know how to act.” I wasn’t sure if I could or should finish the 30 dates, because my heart was not in it anymore. But I pushed myself to finish because this is the toughest part for me when it comes to dating, the in-between. That part where you go from a casual friendship to having good chemistry, to liking the person. Suddenly you’re caught somewhere between dating and a relationship, and the lines of what is appropriate to do or say become blurred. Has anyone read the stupid rule book???

“Just be yourself,” was the constant piece of advice I received from all my coaches throughout this challenge. That’s not hard, I can be my self, at least for the first two or three dates when there’s not much at stake. I go out with a guy two or three times and it’s cool because everyone is just being “themselves” right? But what happens after the fourth, fifth or tenth date? Should I still be myself? Because let me tell you what that looks like… Friendly and honest, but slightly neurotic. Confident, driven and also insecure. Fun and kind, but sometimes awkward. Slightly guarded and defensive, yet optimistic and spontaneous. At some point, I go from being fun, outgoing and cute, to doubting my moves and feeling scared. And I’ve been asking myself, why is that? Perhaps it’s because…

# 2 – I jump to conclusions

We’ve all had these crazy moments in our lives where we lose our “cool” over someone. They don’t call back and we get a sour feeling in the pit of our stomachs. They don’t text back for hours or maybe days, and we start envisioning the reasons why they might no longer be interested. This is what goes on in my head: Maybe he’s seeing someone else who he likes better, or maybe he’s no longer interested in me. For most adults who have been dating longer than Justin Bieber’s been alive, this lack of response from the person we like triggers the defense alarm inside our hearts. Code red flashes through our veins alerting every part of our body. The message is loud and clear: “Close the gates!” “The British are coming!” “Abandon ship!” Whatever the phrase of choice, it means only one thing: Play defense!

And so what I do next may be my own self-fulfilling prophecy in the making. I close the gates to my heart once more, search for ways to combat the feeling of exasperation, and look for things I can control. To some people this means revisiting the roster and going out with other prospects again. For others, maybe getting hammered and then calling an ex, I’ve NEVER done this by the way…

I back away, text less, stop calling and sit inside my fort until he calls again. And if/when he does, I sometimes let my guard down again. But sometimes he doesn’t call or text as often either, maybe because my gut feeling was right, or maybe because my defensive response to what could have been him “taking things slow”, might have caused the same alarm to go off in his head! Maybe he read my signals as a sign of retreat and called his troops home.

# 3 – I care too much

When it comes to dating, I still care too much “too soon”. Am I alone here? Is there anyone else out there who has the same problem? Because maybe I did learn something… I learned that it’s all fun and cute until someone catches feelings. While on a date a few days ago, the guy, his dog and I got caught in the rain as we walked back from the coffee shop. “It’s not the rain that will get you sick,” he told me laughing, as I ran for cover, “it’s the virus in the air.” What a perfect parallel, I thought. “But that’s not what my mother and grandma told me!” I said back, from my shelter under a tree.

Maybe these women had it right, and this simple cautionary tale was meant to be a lesson on love and life: “Be careful about getting caught in the rain for too long, because there might be serious consequences.” I admire my date’s ability to walk through the rain without flinching, maybe he’s not afraid of catching something because his immune system is ready to play defense as soon as the virus hits. Whatever his reason, I’m slightly jealous that his hair doesn’t expand three times with the humidity.

So maybe the lesson is this, if you get caught in the dating rain, you’ll be okay, as long as you can get home quickly and dry off. Translation: if you catch feelings, it’s okay as long as you don’t invest or care too much “too soon”, which is usually my problem. If you stay outside for too long, you might catch something! A virus that will make you sick to your stomach. You’ll get a throbbing pain in your gut that won’t go away with Advil. It won’t help that you drink hot tea, and your mama’s whiskey, lemon, and honey remedy. You’ll be sick for days, sometimes weeks. But like a child who touches a hot stove, you’ll learn the lesson. And the next time you get caught in the rain, you’ll run like hell and find shelter. Or at the very least you’ll bring along an umbrella and some fabulous rain boots.

# 4 – I can’t avoid the butterflies

I can’t  help it, the bug will always get me, I’ll rarely remember to bring an umbrella, because that’s not who I am. I’d rather feel the rain drops on my skin, even if I know that around the corner there might be a virus lurking, waiting for me to let my guard down. I’ll never stop wanting to love or believing in love. But I’m definitely afraid, more cautious, and normally wear my trench coat on rainy days. The problem is that when you wear a trench coat in the rain, you can’t feel the drops the same way. I’m constantly worried about getting wet now, and when I forget my coat, I run as fast as I can for cover, while secretly enjoying the way the drops feel on my bare skin. The problem is, I can’t shake the feeling that I’m going to get sick the next day…

# 5 – I second guess everything

Once I care about a guy, I start second guessing everything because the stakes are higher. I have officially put my heart on the line, I’ve caught the bug, I like him and I’ve let my guard down. But if he’s not on the same page, I’ll be left standing outside in the rain without an umbrella. Sure, I’ll recover after a few days and several  shots of syrup, but just because there’s a cure for a sinus infection it doesn’t mean anyone wants to get one!

The problem for me begins when the guy is not clear or honest in his delivery. The ambiguity makes me very nervous. “You’re GREAT at communication, as long as he gives you the same honesty that you give him,” writes my coach Kevin, who’s known me since I was 17. Great! There’s only one problem, I can’t control the way a guy communicates with me…

“You can borrow my movie if you’d like,” my date tells me, a couple days ago. I smile awkwardly but can’t find a reply, because I don’t know if borrowing a movie from someone who I just started dating is a good idea… Is he saying he expects to see me again? Because surely he wouldn’t want to give his movie away. “Or we could just watch it together,” he tells me with a smile, after I give him no response. Phew, now I know how to answer… “I’d like that,” I say back to him. 

But no matter how he delivers the message, I still get nervous, and I end up sometimes saying the wrong thing or giving an awkward response because I don’t want to seem too happy about the fact that he wants to hang out with me again. I want to be me, but if I’m entirely me, I’ll be all: “Yeah, let’s watch the movie together this weekend, I’ll make homemade popcorn!” For some reason that feels like it might scare him off, although it’s truly what I want to say, I’m just afraid it’s too soon to say it. 

Again, could somebody please tell me where the freaking rule book is? And who wrote it anyway?

Maybe that guy on date 29 had it right… maybe we are all crazy, especially the Mexican ones. But that goes for both women and men. The truth is we’re all so broken up inside, that all our insecurities shine through as soon as we realize we care about someone. When a guy I’m dating doesn’t call or text, it brings back the memories of my high school boyfriend, who I waited for on my front porch for hours so we could go out on a date. He never showed up to pick me up, and the next day he called to break up with me, he had found someone better. And so I’ve learned to be afraid, the stove is hot and I’ll get burned if I touch it. 

I bought a home, I have a great job, I speak two languages fluently and I have an MBA. I’m an independent 30-year-old woman, who is friendly and kind of nice! But when it comes to dating, I sometimes get lost in the questions and lose my confidence to find the answers. “Hey can we get to know each other before you decide I’m too much and run away?” That should be my first question when I meet a guy. Because I refuse to pretend to be anything else than who I am. I’m not a cool girl!

Remember what a cool girl is? She never complains, she doesn’t cry about silly things, and she definitely never gets caught in the rain without an umbrella. Or if she does, she’s probably wearing a white t-shirt… “because cool girls are above all hot”, and wear a D cup.



  One thought on “What I learned from going on 30 dates in 30 consecutive days.

  1. Colleen McGraw
    November 9, 2014 at 4:19 pm

    Still learning these lessons myself, and never completely mastering them. But there are other huge takeaways I hope you are claiming. I admire you; you set the goal to push beyond your comfort zone and you did. You met men with potential and identified some characteristics you did not find appealing. You proved that an open heart is a choice. I hope you always stay with that choice. I hope I can, too. Win-win, xo

    Liked by 2 people

  2. Mónica
    November 10, 2014 at 1:00 am

    I agree with Colleen, I think you learned to just go for it and meet new people out of the blue, some are going to be friends and others not. In the process you also learned more about yourself, what you value and what you may be looking for. The more people you give yourself the chance to meet, the more likely it will be that eventually you will find a special someone.
    I thought about this TED talk as I read your post. I hope you enjoy it and get more comfortable with being vulnerable. Because not everything has a rule book, and that’s actually a good thing. XOXO

    Liked by 2 people

  3. Mónica
    November 10, 2014 at 1:03 am

    …and D cups are way over-rated. Just ask grandma 🙂


  4. November 10, 2014 at 2:07 am

    #18 and 24….Keeping up with the trainer.

    I don’t even know where to start. You know that sickness…that feeling in your gut….that feeling of the unknown that you talk about? Well that’s the feeling I got when I kept getting brushed aside. Imagine that feeling times ten when you come across your story online for all to see. I commend you for setting a goal and completing it …..just realize, this doesn’t just affect you. When I met with you the first time I said to myself “this is the first genuine person I’ve met in a long time”. It was kind of refreshing to say the least. After the second meeting…when you whipped out your card to pay. It showed that you respected the fact that I work for my money just like you do….so yeah I was taken back by it. I thought to myself, two for two! I was looking forward to date three. Maybe we could spend more than an hour together this time so we could see if there was something there. After being brushed off several times I decided to google your name and found that I was nothing more than an experiment. How’s that for got wrenching? Anyway….I hope that you got everything that you wanted out of this experiment. I wish you the best…and I do mean that. I think I’ve completely lost all faith in people but I’m going to keep moving on. Good luck in your ventures!


    • Chelle
      November 10, 2014 at 3:34 am

      I have to say, as woman and someone who has followed this blog, I think, Mr. Trainer that you’ve missed the point. Dating is an experiment. Whether it’s written about online or discussed in private with friends, dating is a personal journey where more often than not, one side ends up more attached / attracted than the other. (Which it sounds like, is the case in this instance.) The posts and the blog are in no way a personal attack or judgement of you or your character. In fact, you could have remained anonymous forever, had you not used your name within your comment. Whether after 1 meeting or 10, any woman has the right to decide when or if the attraction to a person is worth additional investment. I also find it hard to believe that, despite your stated attraction to our friend here, that she was the only person you were dating and considering your feelings about at the time. I’m sorry it didn’t turn out to be everything you hoped it would be, but I find the honest description of her journey refreshing, brave, insightful and… having been there… very. VERY real. You haven’t been “used” you’ve been documented. The experience has been observed and evaluated for what it was, that’s all. From reading, it sounds like your interactions would have ended the same way, whether it was written about and published or not.


  5. Majj
    November 10, 2014 at 6:22 pm

    I have to respond back you “Chelle”, as I think you and “not the cool girl” have totally missed the point. First, I must say that the title of this blog couldn’t be more spot on. In addition, I think a more appropriate title for this “journey/experiment/adventure” should be something more along the lines of “How can I find 30 people to judge in 30 days”. I can’t believe your mother would think anything about this was a good idea — especially a trip to NYC — wow. That speaks volumes as to what values you were brought up to deem as important.

    While I can honestly say that the statement “you can meet a freak anywhere” is completely true — this proves that online dating us a scapegoat for people like you. You didn’t step out of any “comfort zone” — you set out to seek attention from 30 random people. You weren’t honest (completely going against the advice of your “coach Kevin”) …and you jumped to all kinds of “conclusions” in spending limited amounts of time with people in order to form your “judgement” and decide if there was any kind of “chemistry”. Developing a meaningful relationship takes time — not just a breakfast or a fancy meal at someone else’s expense. I honestly don’t know how you kept everyone straight — but hopefully now that your mission is accomplished you can get back to your laundry and refilling that ‘fridge.

    I can only imagine how your insecurities and self doubt would be reaffirmed if you randomly came across one of your 30’s” review of you. My guess is you wouldn’t put any of that up on a blog for everyone to “learn from”.

    And honestly, I have to say that I’m glad you had no chemistry with “The Trainer”. He deserves someone WAY better than anything you have to offer. Epic fail on your part — huge.


    • Mónica
      November 10, 2014 at 6:44 pm

      Wow! The hatred out there! Not quite sure what Majj’s problem is with you going to NYC. Talk about passing judgement! Not that it’s any of your business “Majj” but NTCG went to NYC to help me, her sister, take care of some important business that my husband couldn’t help with because he is terminally ill. Maybe you should take your own advice and not jump to conclusions. She did me a huge favor and met a couple of friends in the process, nothing wrong with that. On top of this you are insulting my mom???? Let me remind you that this was an experiment to meet a variety of new people, why would my mom feel there is a problem with her adult daughter meeting people?? Again, maybe you are judging and assuming that there was more going on. But that’s your problem, not NTCG’s. I can understand if you feel hurt by whatever description NTCG may have posted about your date. But none of us as readers know who you are, you should let it go and not attack people you don’t know.


  6. One of the thirty
    November 11, 2014 at 4:24 pm

    A bit surprised, but I feel more sad for you more than anything else. It seems that you are still wounded by the past or have become numb to the intimacy that comes with dating. Lesson one that you should have learned.

    It’s even more sad that your online persona will triump your actual feelings in the real world. Evident by you continuing this even in actually finding someone of interest. Lesson two.

    And lesson three. You definitely need to check your moral compass. At somepoint you must have had a realization that you cannot truly be present in a date when your thoughts/perceptions/conversations are already translating into the blog during that time.

    Lesson four. Maybe a break from dating would be best for you – invest your time wisely. Go for a run, take an art class, invest in your present relationships etc. Don’t waste the time of others for your personal gain or for that extra social media follower.

    To the trainer, don’t lose faith!


  7. scootergirl
    November 11, 2014 at 8:08 pm

    i loved reading the recap to each date you had. You reminded me how tough the dating scene is 😦 C’mon no one in their right mind would RAISE THEIR HAND and volunteer to jump back in that pool. It’s very confusing and you reminded me of several situations i’ve been in before. To the others that have commented negatively, these are classic tales of the dating scene which we have ALL gone through. No one’s identity was ever given; just the author… so relax a little.

    Liked by 1 person

  8. November 11, 2014 at 8:27 pm

    Everyone, thank you so much for your comments! Monica, that Ted talk was spot on! Vulnerability is such an interesting topic, and one that I hope to explore further on this blog. To Kevin and “One of the thirty”, I’m sorry you’re both feeling hurt because I decided to share the details of our dates. I think you are both nice guys and wish you the best in your own journeys. I already run, work hard, volunteer, mentor, and spend time with my family and friends, but thank you for the suggestions on the other great things I can do with my life! And “Majj” I commend you for wanting to defend your friend Kevin, you’re right, he deserves a good woman, and I hope he finds her some day. I do wish you would all have spent more time reading my entire experience before coming to such conclusions, but I’m sure you had better things to do.


  9. FreshMints
    November 12, 2014 at 3:05 am

    This journey has been brave, self-critical and in no way self-serving. NTCG has taken what is usually so private and allowed others in to be a fly on the wall. She is allowed all of her perspectives. She freely analyzes her own motivations and takes great care to protect people’s privacy and well-being.
    “You own everything that happened to you. Tell your stories. If people wanted you to write warmly about them, they should have behaved better”
    Anne Lamott

    I really appreciate reading this. As someone who has been with the same person for 14 years and did all the wrong things when dating (getting to involved too fast, etc), I have never fully understood the struggles of dating. Being crazy worked out for me. I now see how it’s so hard to gauge how far to put yourself in and how that has not worked out for you (yet) and so many others. My point is, yes, I got lucky (so, so lucky), but I think there is something to be said for following your heart and going all in at some point, even if it might end badly. You can’t change your passionate, caring nature!

    You don’t have to find 3000 great guys that fit you, or even 30. You just have to find one. So onward. And upward, if the comments above are indicative of the past!


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