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25 Things I learned from 25 First Dates

Going on 25 First dates was an adventure. I learned a lot about myself, men, and dating in general. All in all it was a good experience.

Going on 25 First dates was an adventure. I learned a lot about myself, men, and dating in general. All in all it was a good experience.

I have to admit that I was kind of naïve when I went into my online dating experience. To some extent getting dates was easy. Figuring out what to do with them—not so much.

On my 25 first dates, I met a lot of great guys and some I went out with several times. Some I met once and never saw again. Others I still am in contact with. I can’t say it was easy though to put myself out there over and over. However, I believed in myself and in the process and I was willing to show up and try.

Dating takes up a lot of mental energy and time and gives no promises of ultimate success. Overall, I have no regrets and I really did learn a lot about myself and men in general. Hopefully, I can put that to good use for the next round of dating. Until then, here are the things I learned from my 25 First Dates.

25 Things I Learned From 25 First Dates

Men are people too. They have their own hopes, dreams, feelings, and share of insecurities.

Men use old pictures. They also overestimate their fitness levels and how young they look. It’s kind of a crap shoot what you’re going to find on your actual date. To be fair, this happens both ways I’ve been told. Just realize that it’s really common and try not to look too shocked. I totally get feeling young at heart—I do myself. But I still am truthful about my age and use current pictures.

There are good guys online. This was a nice thing to find out. Actually, all of my dates were polite, paid for the date, were intelligent, and were pleasant to be with. They had jobs, knew their manners, and for the most part will make someone a nice partner someday.

There are not so nice guys and quite a few fakes online. Some fakes are easy to spot with a fake picture and stilted language. However, there are some that are more sophisticated and use pictures of a normal looking guy and a fairly normal sounding profile. There were a couple that I wasn’t sure of until we exchanged a couple of messages. You have to use common sense and caution. If you feel any doubt or uneasiness, I recommend moving on. Why chance it?

It seems like most of the men I have met, have been burned by exes or dates. They are extremely cautious when dating. Maybe too cautious if you ask me. Most of the men I went out with had been single for many years, 5–24. Most fell somewhere in between. Several men were quite committed to never getting married again. As someone new to dating, I didn’t care that much about potential marriage. But it’s sobering to think about.

Guys want you to have your act together. See above. As cautious daters, they really do want a woman who is self sufficient, a lady, knowledgeable, and has a social life. A man who is hardworking and careful with his resources will expect the same from you.

There is no perfect way to meet someone. I started out with meeting for coffee. That seemed safe and low commitment. I avoided anything with alcohol such as meeting for drinks. After some time, I loosened up that restriction and have tried meeting for lunch, wine, or dinner. They all have their pros and cons. So, since I’m kind of old-fashioned in letting the man ask me out—I will leave it up to the person asking. That has the advantage of keeping first meetings somewhat fresh.

I had to get comfortable with rejection and not take it personally. It is personal though, because someone is saying they don’t want to date ME. So, even though it is personal—you can’t take it personal. Yet, my ego hates to be rejected even when I would know it was for the best. It still doesn’t feel great.

As bad as being rejected is—I hate being the rejecter. I still need to learn to reject, say no, and move on as needed. I hate doing that and actually found it easier when the guy would do it so I would let things go on a date or two too long just to be sure. Trust me on this, if you feel that way, sooner is better than later. Do as I say, not as I do!

Sometimes you’ll hurt someone. That’s not fun either. See #11.

You will learn a lot about yourself.

It’s hard not to become jaded and discouraged at times. Take breaks as needed. I’m on hiatus now from dating. When I found myself just going through the motions without any enthusiasm, I knew I needed a break.

Some dates will evolve into friendships. That has been a pleasant surprise. I made some friends that I wouldn’t have otherwise. Two of my former dates have evolved into good friendships that I enjoy to this day.

I was introduced to hangouts that I love to this day. That’s how I found my favorite coffee shop and wine bar in Houston.

Guys really aren’t expecting anything physical on a first date—not even a kiss. It’s odd but when I first meet someone from online, kissing or anything else is the last thing on my mind. It’s always a little awkward and you are just getting to know each other. It seems men are the same way. Out of 25 dates, I never had one man try to do anything inappropriate.

There is always a little disconnect between the guy you’ve been getting to know online and the one you meet. That’s okay and normal. When you are talking to someone online, your brain gives them a voice and some kind of look. This will NOT be the person you meet. So, part of a meeting is spent trying to recalibrate your image of this man. If you make it to a second date, it feels much better and your imaginary man disappears.

Even when things seem to be going well, some guys will just disappear. Again, this is something common. It can be because of so many reasons none of which you’ll probably ever know. When I did have a chance to find out, it was usually another woman. Accept and move on.

Don’t assume that because someone has a profile up, they are ready to date. I thought knowing how long they had been divorced was the important thing. Not always. It’s also important to know how long they’ve been out of their most recent significant relationship. Just because someone has an active profile, they may still have attachments to someone that they’d like to date again.

Sometimes when you think you’ll never see a guy again, he may resurface. You can take this on a case by case basis. From a romantic standpoint, for me, it has never amounted to anything lasting. However, the two friends I made came about this way. Obviously there was some connection—it just didn’t turn out to be a romantic one.

I had to learn not to overthink or read too much into messages or texts. For someone like me with an overactive mind and imagination, I had to learn the hard way. If someone is making plans with you on a consistent regular basis, it’s probably good. Don’t get too caught up on the number and timing of texts.

I learned a lot more about what I liked and didn’t like in men; about what was and wasn’t important to me; and sometimes these things surprised me.

I enjoyed dating when I was more open. As I went on, I got pickier and more guarded but I don’t feel like my experiences have been as good. For example, in the beginning I was open to all ages and I met men from the age of 45 through 67. I went out with heavy men and thin men. I went out with men from different backgrounds and in different professions. And I enjoyed those dates! Now that I think about it, that period was actually more fun than when I started focusing on what I thought my “type.”

Most men know when you are playing games. Most men know when you are feeling desperate. The best advice I can give is to live your life fully and be honest in your interactions. The key to having a good relationship is truly being the kind of person you would want to date.

I’m discovering that my natural speed of getting to know someone isn’t super conducive to the lightening speed in which minds are made up on a first date. As a very private person, it takes me a while to warm up and really be myself. It doesn’t usually happen in the first meeting.

I have a tendency to want to fix things about myself in order to please other people. But my goal for 2016 is about accepting myself and believing that there is someone out there that will accept me too. The fact is, I know a lot of imperfect people who have relationships that are perfect for them. Perfection is not required to find love.

Going Forward

As I said at the beginning, men are people too. They have hopes and dreams, feelings, and their own share of insecurities. I’m trying to keep that in mind even though I tend to focus on how all of this affects me.

Like anything else, there is no way to learn or get comfortable with something except by doing. I don’t know if my way is The Way…but it was something of an adventure. I’m glad I gave it a try and I certainly intend to give it another shot.

Keep showing up my friends! Got any dating advice? Feel free to leave it in the comments below! I need all the help I can get. 🙂

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I'm a former counselor, career services leader, and college advisor. Now I coach and write at My Think Big Life promoting health and personal growth.
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