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Dating : Advice for the younger, almost 33 here and looking grim

Dating : Advice for the younger, almost 33 here and looking grim


So I never got good advice from my family and friends. I always heard « It will happen when it happens. » or « Shes out there and will find you one day. » or some other fairy tale nonsense/super lucky person if it happens for you stuff…

Here’s my ADVICE -> You need to ask them.

TL:DR – Ask out anyone you’re interested in, especially if they are showing any type of interest in you, because by the time you are my age the options are very limited.

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Don’t be scared or shy, take the chance! If it fails, you’ll feel a lot better knowing you won’t be wondering « What if? »

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Want proof?

Here are some quick stories of my mess ups! The 3rd story is my biggest mistake and the worst.

Story 1:

In high school, it seemed like no girl wanted to date me other than two I didn’t find very attractive. They were both very adamant and forward about wanting to go out with me. Both were freshmen when I was a junior and when I was a senior one of them followed me out to my car and wouldn’t let me leave till I gave her a kiss… I am just now realizing how messed up this is… I was too polite and friendly… but dear god. She did have guts, gotta give her that. I did give her the kiss.

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Anyway, fast forward and I am 24, bar hopping downtown in the city about 35 mins from my home town, and I run into some of the ladies from my time back in high school. They instantly shout my name and I have no idea what their name is but I recognize them. I asked them how they knew my name, and they told me « Everyone knew you and your brother’s name. You were the two hot twins! Everyone wanted to date you! » I am shocked and ask « How come no one ever asked me out then? » and I get « We were too scared! »

So apparently I should have asked out more chicks in high school…

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Story 2:

During my freshmen year of college I had this very large roommate who was one of those people who can bullshit and talk his way through anything. He knew everything and everyone and could always entertain people with his lies… He was also the worst roommate ever, not just what I said, but everyone on my floor said. He would always have the TV at max volume while listening to music on his laptop out loud. He would use my towels, cereal bowl, spoon, and other items. He would blow his nose with my hand towels (which I just gave to him), and eat my food! He would stay up till 4 A.M. have his lap top playing out music and would get mad when I asked him to put on head phones. He’d have his alarm set for 6 A.M. and he wouldn’t snooze it nor would he wake up for it! (He missed so many classes he was on academic probation after the first year.) He also didn’t smell the best.

Anyway, so I left every day to work out. Many times I would run back without a shirt on. Anyway, the chicks noticed and they were attracted. A bunch started to add me on facebook and unfortunately I was really really stupid. I didn’t know who they were so I would just decline them… After about a month of this, I told my brother and he told me how stupid I was…

Then one day a group of these ladies, from the dorm connected to ours, show up at my door. I’m sitting there playing computer games and I wanted to get back to my computer games… (huge mistake). I also thought they were all there to talk to my roommate because I didn’t invite them over… So after saying just a few words to them, I literally go back to my computer game…

Fast forward a four years (super senior for the win) and I run into this girl with this triforce tattoo on her ankle at a party. So I go « Hey you like to play video games? » (Still not very popular amount the woman in this area of the country.) and she looks at me and shouts my name. « Name!!! » and I go « Yes? How’d you know my name? » She tells me that she was one of the ladies who had a crush on me freshmen year and lived in the dorm connected to mine. She then asked if she remembered that time all those girls showed up at my room and I blew them all off. I told her I did. I asked her why none of them asked me out and she told me they were all too scared. She then introduced me to her boyfriend.

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So apparently I should have not been a complete idiot in college and should have also asked out some ladies.

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Story 3:

One day I see this beautiful girl in one of my classes and a few days later she adds me as a friend on facebook! My heart skips a beat and I add her right away. (I didn’t get the hint) We talked a tiny bit but I didn’t want to seem needy or desperate or foolish and I didn’t say much or keep the conversation going. The semester ends and I am bummed since I won’t get to see her anymore other than when we walk by each other by chance.

A year goes by and it’s the start of the semester. I get to my class a bit early and I am the first one there. I sit down down. I hear a person come in and its the beautiful girl. I go back to eyes forward and all of a sudden the chair right to my left moves! She sits down right next to me! There are like 30 other chairs to choose from! My heart races out of my chest and I think about saying « Why don’t you just ask me out while you’re at it? » and another part of me just wanted to fall over and put my head in her lap for some reason as if I was going to take a nap.

Anyway, not much is said. We leave. I wasn’t sure I wanted to be in that major and I drop all my classes and get new classes.

Fast Forward like 6 years. We end up chatting on facebook and I find out we have a ton in common, she wanted to go out with me but was too scared to ask, I tell her « You looked like your schools prom queen! I was too afraid to ask! » She tells me « I was my schools prom queen. » By now though she is married. We’re no longer friends because her husband found out about us talking.

If she adds you on facebook, and sits next to you in class, she is probably into you…

I’m almost 33 and my looks are fading fast. I am in great shape for my age but my hair line isn’t the best. I’m probably a 6 or a 7 on a good day.

Don’t be scared and let your best years ago by; take the chance.

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I hope one of these stories will convince one of you to take a shot.

Thanks for reading.

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  1. I agree with /u/autodecide that you’re in your prime. You seem to have a lot of the ticks a girl would be after too. I’m in a similar position to you, early 30s, decent shape, stay fit, no hygiene issues and interesting hobbies(that I also show in my tinder profile). Looks wise I’m probably a 5.5/10. I’ve been on Tinder for 3 weeks and I’m usually doing 2-5 dates a week, this is a throw away account so no humble brag intended.

    I guess what I’m trying to say is, maybe it’s none of those and you’re lacking in a different area? Some of the girls showed me conversations she has with some of the other guys and they are super weird, like very poor social skills and awareness.

    Do you have a lot of confidence? Girls dig that.

    No offense intended, just offering my two cents.

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