Deca-dating: 10 First Dates in 10 Days. Here Is What I Learned

I have never really dated many people. I got married when I was young and have been in long-term relationship after the marriage ended. When I would meet someone, it was organically and usually through friends. In August this year I decided to travel more and take work projects around the country, and as I took a big leap in my life geographically, I decided to make a change in my romantic life as well.

Enter Tinder. Apparently no longer for hook-ups, this app seemed like a fun way to meet men in the area, especially since only those men that I liked and liked me back could message me.

I joined on Thursday, went on a first date the following Monday and had 10 first dates over the next 10 days. My goal was to say "yes" to life, say "yes" to possibilities and see what happens. Here is how it went and what I learned about myself.

Here were my rules:

1. Stay open to learning more about a person than meets the eye. There is good in everyone, so I wanted to focus on that.
2. Pretend that the person already liked me and act as if we have been friends for a long time, because that’s when I was being myself.

10 things I learned:

1. Don’t let yourself-esteem be affected by the behavior of others. All men will act the way they know how. It has little to do with you. YOU get to choose what you ALLOW.
2. It’s a good practice to go out and learn to feel good in your own skin. Acting natural may not feel natural when you are gaga for someone. So, practice with people you may not have a spark with, yet find interesting. This behavior can help you avoid being nervous and anxious when you do have a strong connection with someone.
3. Don't judge a book by its cover. If you stay open-minded, you may meet interesting people you may have overlooked before. If your gut says there is something wrong or unpleasant about the person, listen to your instinct as well. Even if there is chemistry and you think someone is hot, observe their actions - actions are louder than words and hotter than looks.
4. When you are going out with a stranger, meet in a public place and let a friend or family member know about your where-abouts as well as share the info about your date. You can never be too safe.
5. The number of texts it takes a man to ask you out can be proportional to how enthusiastic he will be on the date. If he asks you out on 20th messages after a week of texting extravaganza, he is probably not that interested. If a man really wants you, he will make it clear and ask you out without delay.
6. You don't have to respond to every text message, especially the ones with simple statements. Dating sites are to see if there is a connection and then the next step is to meet. If a man wants to meet you, then he will make it known. If he just makes a statement, then he may be looking for a pen-pal. So, don't respond and see how he reacts. This can actually really help to weed out men with anger and control issues. How they react when they don’t get what they want early on is a big tip of an iceberg.
7. Always set a time frame for the date and let him know when you have to leave by. If the date is bad, you have an easy way out. If the date is good, it will make you both look forward to more.
8. When you go out with different people, you can avoid obsessing over one in particular. When you have other dates lined up, you simply don’t have time to worry or stress. There are too many in the pipeline!
9. If the person you really liked is not that into you, you can quickly shift your focus to another suitor who does see how amazing you are.
10. You really get a sense of who YOU really are without being influenced by others. The contrast you get between the suitors will show the only thing that remains constant – your own presence. And that’s a great way to get to know yourself and your true preferences without settling.

10 Dates breakdown:

Date #1
Bachelor #1 was the first one to respond to my flirty line in my profile, in which I said I was always on a search for the best gelato in town. In his third message to me he offered to take me to a place that had something better than gelato – rich, locally-made ice cream. How could I say no to that?

I haven’t been on a date in months, so naturally I was nervous. What if he doesn’t like me? What if I don’t like him? What if he is shorter than I expected? What if he is a psychopath? Ooh, good thinking! Just in case, I texted his contact info and photo to my best friend.

Despite his cheerful profile, bachelor #1 turned out to be a bit of downer and not as positive about life as I expected him to be. However, since that was out of my control, I quickly brushed off that thought and decided to focus on one thing that I could control – being myself. But what was that, exactly? Do you ever feel like you are a different person depending on who you are with? That has been the case for me most of my life. However, since I was making big changes, I decided to try something new – just be myself. To do that I imagined that this person liked and accepted me as if we have been friends for years. What a fun idea and it worked like a charm!

I immediately relaxed and started to pay attention to the moment. I also stopped obsessing whether he liked me or not. In my imagination, he already did. After an hour chat over ice cream (which was delicious), I noticed that he was doing most of the talking, barely giving me a moment to respond. I believe in conversations, not monologues and didn’t love that energy, so I said I had to go. My date walked me to my car and asked for a kiss on a cheek. I politely agreed, got in my car and left.

He texted the next day to check on me, but didn’t ask me out again. Phew.


Date #2

Bachelor #2 messaged me asking if I needed a boyfriend. I playfully said that I don’t “need” anything, but can be charmed by someone to reconsider. He loved that I was in the "not-needing" zone and in his second message, he asked me out for gelato in my town. We met on Tuesday night at a little Gelato shop. I enjoyed a fun Rosemary-Vanilla flavored gelato covered in milk chocolate and hazelnuts. He admired my adventurous spirit yet picked a safer dark chocolate flavor for himself. He asked if I wanted to go for a walk and we had a fun time chatting and strolling around town. I didn’t feel great sparks and he wasn’t my usual type, but I liked the guy.

He offered to walk me home, kissed me lightly goodnight and immediately asked me out for a second date. He also texted me 10 minutes after the date to say it was nice meeting me and he was looking forward to seeing me again. This is fun!


Date #3
Bachelor #3 was a world-traveling yacht expert who lived on a boat in a nearby marina. He asked me for my number in his second message and called the next day instead of texting. Very refreshing! Even though he looked much older than I would like my partner to be, I still agreed to meet him, as I was staying open and was willing to see what the universe had in store for. Besides, I could always make a great friend with a boat!

We met at a juice bar nearby on Thursday morning and chatted for 40 minutes over a dragon bowl (think healthy ice cream for breakfast). Even though I didn’t feel any chemistry, once again I kept reminding myself to stay open and be myself. This was good practice to act as if I was loved and adored. An hour after the date, Bachelor #3 called me to say he registered for the same meditation retreat I told him I was going to later in the month. By going out on this date not only did I make a fun friend with a boat, I also expanded my circle of spiritual friends!

Date #4
Bachelor #4 was a hot, mysterious-looking magazine editor and writer. I loved how he wrote me long messages and how eloquent he was with his words. Big turn on. However, unlike the first 3 guys, this one took the longest time to ask me out. Technically, he said “if you want a guide, I’ll be happy to show you around…” Yet later it was me who suggested checking out a place he mentioned earlier. So, wait, did I ask him out?? Not a good sign. When we met, he didn’t seem too excited and didn’t even give me a hug or a kiss on a cheek. During the whole date, I felt like I was “making” him go out with me.

But here is the cool thing – because I just went out on 3 dates before and had more lined up, I knew that this guy’s behavior had nothing to do with me. He was being himself. His aloofness didn’t have to mean that I wasn’t worthy or that I wasn’t likable. It just meant that I may not have been his type, or whatever. Because I strengthened my “being myself’ muscle, I felt much more at ease than I would have been, if he was the only date I had lined up.

At the end of the date, we partied on the street with him saying – “well, this is my street. Thanks.” Then he turned around and walked in the direction of his home, leaving me on an empty intersection at 11pm. Hmm… Guess I won’t be hearing from this one.


Date #5
Bachelor #5 asked for my number in his fifth message, however I didn't hear from him until 4 days later - Friday afternoon. Because of all the earlier dates, I actually decided to take Friday off and didn’t make any plans. Around 4pm he texted me that he was going to be in my area later that night and asked if I wanted to meet up for a drink. Because he was hot, I conveniently ignored my “how dare he ask me out so late!” thought and say yes. What the heck, right? I could use a glass of bubbly.

Here is a big distinction: while he did say he was enamored by me and has stalked me on Facebook, his actions showed the opposite – he asked me out last-minute, which clearly indicated I was not a priority to him. This was fine with me, because I haven't invested my time and emotion into him yet. However, it would have been disappointing to be treated this way by someone if I had big premature plans for the relationship. Luckily, because I had other dates, I didn’t obsess over this one.

When we did meet, we hit it off, chatting non-stop for an hour about our mutual interests in meditations and travel. He walked me to my building and asked me if he could kiss me. I said yes and man, oh man, was that kiss something. Not the light kind like bachelor #2 demonstrated, but the passionate and strong. He even pulled my hair, which got me a little weak in the knees. He texted me within 10 minutes saying that he could have kissed me all night. Yum!

But guess what? I haven’t heard from him after that night. Just another reminder that quick moves and charming words are a lot of hot air (which can be fun once in a while too). Good lesson.


Date #6.
Bachelor #6 messaged me about once a day and asked for my number in his forth message. However, I didn’t hear from him until Friday night when I was out with Bachelor #5. The following day, I replied to his text saying I was going to be out in my town for drinks with friends, if he wants to meet up. To be honest, I wasn’t that interested in this one, but he seemed nice and I figured there was no harm inviting him to join us. He did come to meet us and we spent time chatting at the bar.

Even though I was still being myself and acted as if he was an old friend, he somehow felt different about this first date, so he put his hand on my knee. Hmm… I didn’t like that. Obviously our energies were out of alignment - I didn’t give him any signals for that and he didn’t ask if that was Ok. Red flag! Through out the night he kept putting his hand on my back and leaning in way too close. It felt a little too touchy-feely for the first meeting, which I didn’t care for. However, when he walked me home, he simply gave a kiss on a cheek, which was sweet and very gentlemanly.

He called me the next day saying that it was nice meeting me and that he hoped to see me again soon.


Date #7.
The following morning I woke with a headache – too much going out, too many glasses of bubbly and too little sleep. However, I had a smoothie date with Bachelor #7 at noon and I was committed to this dating thing. I also knew I could use a green smoothie. Luckily my date was running late, which gave me an extra half hour in the morning. He actually texted me an hour before the original meeting time to let me know about his late arrival, which I really appreciated.

This guy was different from the other men I have gone out with so far – he was a chef, like me, but while I am all about flowers and butterflies, he was all about tattoos and piercings. He looked like a badass. Or at least that’s what you would see outside. But because I was staying open and listening to how people showed up when they wrote, spoke and acted, I was curious about meeting him.

His first message to me was to introduce himself, point out our common interests in cooking, meditating and dogs and suggest that we should be friends. That put me at ease and re-confirmed my new belief that in order to act truly natural, you can simply imagine that the person you are with as your friend. We texted over the next few days with quick little hellos and in his 8th message he asked if I wanted to meet.

Not only was this guy kind and interesting, he also had lots of depth. I was very inspired when he said he taught weekly meditation to prisoners. Wow! I wondered what would have happened if I wasn’t open-minded to this dating thing. I would have just pushed him away with my pre-conceived stories of how people “are” based on what they look like.

We ended up talking for 3 hours and could hardly stop. He messaged me within 30 minutes after the date saying how much he enjoyed meeting me and that he wants to see me again. He also said that he was interested in more than friendship and I liked this directness and honesty.


Date #8.
Right after my date with Bachelor #7, I had Bachelor #8 scheduled at 3pm for juice. This started to feel a little like work interviews! Just like Bachelor #7, my second date of the day was also running late, yet he didn’t give me much heads up. He actually showed up even later. Same situation as Date #7 - two different people. One lets you know about being late in advance, while the other one doesn’t. And it has nothing to do with YOU. You never have to doubt your worthiness. It is all about THEIR standards. Now ladies, you can choose which one of your suitors fits YOUR standards, but that’s a choice you have to make for yourself.

Similar to Bachelor #7, Bachelor #8 was also into meditations and Buddhism. However, his energy was very distant and he didn’t feel present. He hardly looked at me and didn’t seem too happy to be meeting me. Looking back at our messages, I see that he never really pursued me. He took time to ask me out, waiting for a day between short messages and finally casually asked in his 11th message if I wanted to meet. It didn’t feel like he was really that interested.

After about an hour of talking, which felt a little like pulling teeth, he walked me home, gave me a quick hug and walked off to meet up with his friends. None of this was taken personally, as I have learned that everyone is different and their behaviors don’t have anything to do with me.

I haven’t heard from him after.


Date #9
I don’t know why exactly, but I scheduled a third date for that Sunday. Bachelor #9 and I were going to go salsa dancing in the afternoon. This guy also took his time to ask me out and didn’t seem too eager about it. Yet, he was cute, smart and he could dance, so I said yes. He was pretty quiet when we met and didn’t seem too proactive. Just like his texts. Again, the way the guy asks you out can show how he acts in real life.

We had a nice time walking around the city, grabbing a bite to eat and then dancing. Because I was so tired from all of my dating, I had to cut this one short. He walked me in the direction of my building, but left me half-way at the intersection that he had to turn at. We hugged good night and I haven’t heard from him since.


Date #10
Because I overbooked my Sunday, I took Monday off from dating and set my next date for Tuesday. Bachelor #10 asked me out in his 8th message, but unlike all others, he asked me out to dinner, not just a quick meet-up. Since he offered to take me to an excellent Ethiopian restaurant, I said yes. Heck, if the company wasn’t great, I knew the food would be. He was good looking and seemed very interesting and well-traveled, so I figured I may learn something new about the world.

I did see a big red flag in his texts. On Saturday afternoon he messaged me apologizing for a late notice due to lack of Tinder notifications and said he needed to reschedule for Tuesday from Saturday (which was the original date.) Here is my thought - if someone is thinking about you and wants to meet you, they will check the app! They will find a way to get in touch early if they need to reschedule and not wait until the day of. Clearly, he wasn’t that concerned about my plans.

This tip of the iceberg of not thinking of me proved to be right. The whole dinner he talked 95% of the time. He asked only 3 questions about me and carried on the conversation as soon as I finished my answer. I prefer dialogues and not monologues, so this guy wasn’t for me. Funny enough, he thought I was great and when we parted ways in front of the restaurant, he said he would like to see me again.

However, he didn’t offer to walk me to my car, which was another red flag for me. A real man desires to protect the woman he is with, and this guy didn’t seem to care about anyone but himself. He texted me within an hour saying that he would like to see me again and try my vegan lasagna. Wait, did he just ask me to cook for him on a second date?

I laughed about the whole dating experience on the way home and made a decision that I had enough practice dating and being myself and now needed some rest before my second dates! And so the dating adventure continues :)