26 Things I’ve Learned About Dating


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This weekend I celebrated my 26th year on this earth and I’ve been struggling with how I feel about that. On one hand, I think it is possible that this will be the best year of my life. I’ve got this fantastic new job, I’m in the best shape of my life, I’m moving to Del Mar, and I have truly amazing friends and family. On the other hand, when I look at my dating prospects… I got nothing. It’s frustrating and I can’t help but feel anxious about my lack of progress in this department.

But then, today, I started thinking about progress in a different way. Sure, I am not currently in a great relationship and I may be nowhere closer to a happy marriage and family BUT I have definitely moved forward. All of these failed relationships have made me more self-aware and have taught me so much. And I have to believe that all of these lessons I’ve learned will only make it easier for me when I do meet the right guy.

So in honor of my birthday, I thought I’d list out the top 26 dating lessons I’ve learned in the past 26 years (in no particular order).

1. Making someone jealous is only good in theory - Over the years, there were many times that I flaunted another guy’s interest in me in front of the guy I was dating to gauge his reaction. I’ve found this is a good way to see how interested that guy is in you but it comes at a price – paranoia, jealousy and eventually fights. Turns out there is a better way to find out if he likes you –  ask him.

2. No strings attached is a myth – It sounds like a good idea, but it never pans out. If the guy isn’t cool, then you feel like shit for lowering your standards. If the guy is cool, then eventually, you are going to feel like shit that he only wants to make out with you.

3. You can in fact be friends with an ex, but it is a very delicate situation – I have gone back and forth on this one and have even developed my own set of rules for hanging out with an ex. But now that Mr. Cute but Whiny and I are legit friends. I can’t deny that it is at least possible.

4.  Facebook has made dating 10,000 times more complicated - Every post I’ve done about Facebook and dating has gotten thousands of views, which tells me that I am not alone in feeling confused by dating rules and FB. It’s all messy… everything from how often can you write on your boyfriend’s wall, to dealing with the Facebook break up and then the eventual defriending. The rules are always changing and we are all struggling to keep up. At least we can commiserate!

5.  You aren’t always right - This is a hard one to swallow. I’m working on it.

6. You aren’t alone in dating angst – The one thing this blog has taught me more than anything is that there are a LOT of people going through challenges when it comes to dating. I’ve loved reading everyones comments and tweets because it makes me feel much less depressed.

7. Most guys won’t dump their gf’s no matter how unhappy they are - Dumping makes them the bad guy and they really don’t want to be the bad guy. So if you like a guy, and he has a GF that you know he doesn’t like, don’t hold your breath waiting for him to be single.

8. A lot of guys say they will call when they won’t – I’ve gotten thousands and thousands of searches leading to my blog for the term “why hasn’t he called?”  Clearly, its a mystery to us all. (Hint, guys, try calling a girl every once in a while. It will probably well received…)

9. What you say and wear on a first date is imperative. Do not take preperation lightly – Guys judge, and they remember. But they are also pretty easy to please. So just avoid anything slutty or awkward an d you’ll prob be ok.

10. Practice safe sex - Between false preggers alarms and serious health risks, this isn’t a lesson you want to learn the hard way. Without getting too “Sex Ed” on you, I can’t count the number of my friends who got HPV from their boyfriends. It is a good reminder that thinking, “it won’t happen to me” isn’t smart.

11. There is an art to the drunk dial - If you want to make out, it’s best to know the rules.

12. Boyfriends come from completely unexpected places - I met Mr. Not Quite Right at my least favorite bar in SD. A bar I usually avoid at all costs but was dragged into on that particular occasion.

13. The key to making a relationship work is a good fit – Everything else aside, the relationship isn’t going to work if your lives aren’t at all congruent. When they say timing is everything, they aren’t lying.

14. Settling will make you feel like shit - enough said.

15. It doesn’t matter who breaks up with who, break-ups fucking blow – I used to think if I was the one to do the dumping, I’d save myself all sorts of angst. WRONG. (Clearly, since I broke up with Mr. Not Quite right and am still, a year and a half later, sometimes sad about it).

16. Guys don’t want to date “one of the guys” - This one is hard for me because I have so many guy friends, but you have to remember its ok to act like a girl around a guy you want to date. The “cool, funny girl” is the girl guys want to be friends with or hook up with. The “nice, sweet girl” is the girl guys want to date. Just because it isn’t fair, doesn’t mean it isn’t true.

17. For all the guys who treat you poorly, there are 10 more guys who will treat you well – So dump the guys who can’t get it right because you deserve to feel secure and happy.

18. There is a LOT of controversy when it comes to the conversation of who pays on a date and apparently there are some very angry guys out there - The 120 comments I got on that blog post, many of which called me a bitch, whore and other savory names, proved that to me.

19. Your exs’ friends are never a good way to go – Sure, it’s tempting, but don’t do it. A. too much room for your ex to sabotage. B. You are going to have to see your ex. C. The friend is always going to be jealous of the ex so there isn’t much potential for a future.

20. We are all insecure in our relationships - I think of myself as extrememly confident. But when I get in a relationship, all of a sudden I second guess everything, even when it is clear there is no reason to. Ironically, it is this same quality in guys that so often annoys me. I think we could all benefit from a little more open communication.

21. It is always better to express your concerns then keep them bottled up – With Mr. Not Quite Right I was too scared to bring up all the things that were pissing me off. So, instead I went the uber mature route of just letting them build up inside of me until I dumped him out of nowehere. Not the way to go.

22. Pick your battles - While it is good to bring up your concerns, sometimes you have to let a few things go. Otherwise you will spend all your time talking and won’t have anytime for fun or sex.

23. Red flags should not be ignored - The things that cause concern in the beginning are often the things you end up breaking up over.

24. Having a boyfriend makes you gain weight - Fact. A combination of a lack of time, a guy’s appetite/diet and the security of being in a relationship, forces you to get chubbier. In future relationships I intend to find a way to stop this and until then I’ll just flaunt my recently 20 lbs thinner ass. Thank you, singledom!

25. Dating online is par for the course these days - Seriously, most of my friends have done it at one point or another, although the only way I know that is because I flat out asked them. Apparently society hasn’t gotten to a point where they are ready to volunteer that information.

26. Being single can be totally awesome – Truly. Right now I am honestly the most happy I have ever been and, gasp, I’m single.

So, there you have it – 26 pearls of dating wisdom from yours truly. I am sure there are many many more lessons to come, but for now I am grateful for what I’ve learned so far. I am also hopeful that I’ll be able to put this knowledge to use sometime very soon 


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