A Brief Memoir and A Few Pointers From A Late Bloomer In Dating

Let’s face it. Approaching and dating can be nerve-wracking. They can especially be so if you’re in your mid to late 20s and have little to no experience with dating and relationships, which seems to be pretty common these days. Whatever the reasons for this, I’ve decided to share a bit of my experience and what I’ve learned about how to approach dating for this week's #BATTLEROYALE.

I wasn’t very social in high school, didn’t go out much on weekends, and didn’t have many close friends. I only talked to girls once or twice a week at my church youth group. When I got to college, it was total culture shock. I went from almost never seeing girls to being surrounded. Add onto that that I was extremely shy and socially awkward – and was the dictionary definition of a “white knight” suffering from “nice guy syndrome” – I didn’t know what to do.

The first girl I liked in college was the cutest thing I’d ever seen (to that point). She was intelligent, bubbly, and outgoing. I wanted some kind of certainty or “approval” before ask her out. I had a feeling that she liked me, but couldn’t tell. I was often switched between excited and frustrated and lonely. I was getting nowhere way too quickly with her. Finally though, I manned up and asked her out. She accepted and we went out for pizza a few nights later.

Now that I've shared about where I came from in this regard, I'll share a few simple points that I've picked up on over the years.

Get comfortable with uncertainty

Okay, so she’s nice to you, she’s excited to see you, she smiles at you and jokes around with you…great. She’s probably the same way with her friends. Don’t project what you think she feels on her and don’t look for indicators that she likes you. You’ll have too much to overanalyze and, like I was in college, end up frustrated and lonely. Additionally, it takes away from the fun – yes, FUN – of asking her out. Think of it like the first time you went zip-lining, white-water rafting, or off the high dive.

Think about it like a game. You don’t know if you’ll win or not, but doesn’t it feel great if you do? Wouldn’t it feel great if you win her over? Know what you want, know what you have to offer, and then go after it!

Getting her alone

The Brief Memoir Of and A Few Pointers From A Late Bloomer In Dating

The “how-do-I-get-her-alone” part? This situation is not fun, but there are ways around it! I found myself in that exact situation once. We had already been acquainted with each other. We had a large group of friends that met at a bar one night. As the night started to wrap up, I spotted her at a table with some of her friends. I started chatting with one of my friends who was standing near her table so that I could get her on her way out.

As she got up to leave (along with everyone else at her table, mind you) and walked right by me, I acted surprised to see her. We caught up for a few minutes. As the conversation went on, I turned my gaze and my posture every few minutes so that I could slowly rotate her away from the group and get their attention off her. Once I saw that, I asked her out and she accepted.

Don’t ask her to “hang out”

You are specifically asking her to spend time with you specifically. You want her to go out with YOU, to spend time with YOU. Don’t ask her to “hang out”. Friends “hang out”. We’ve all heard of the dreaded “friend zone”, right? If you want to stay out of it, then you won’t “hang out” with her. This leads to my next point…

Be bold and decisive!

I sometimes see guys asking how they can subtly ask a girl out, how they can drop hints of interest, or other things like that. I’m not sure how common it is to try this, but you don’t want to do that. Hints and subtlety won’t get you what you want. She’ll either be confused or won’t pick up on them. Plus, even if she does, when will you have dropped enough hints? What will be enough?

Who pays?

If you ask, you pay.

The Moment of Truth

Like I said earlier, asking a girl out can be intimidating. You’ll feel like your heart is about leap out of your chest. You know, kind of like the creature in the movie Alien. So what do you do? Tell yourself a joke. Before you walk up to her, say to yourself “I am not in the movie Alien. I am NOT in the movie Alien…I am NOT an alien!” Humor is a great way to break up tension and help resolve situations, or at least make them less stressful.

After you’ve asked her, you’ll think to yourself “Oh, what have I done?!?” If she says “yes”, then you’ll feel indestructible. Unless you get attacked by a xenomorph, that is.

Eh…those are the creatures from the Alien franchise.

You’ll feel like…well, like this…

Dating isn't as complicated or intimidating as it may seem! That's not to say it's the easiest thing in the world, and I know it may seem intimidating at first, especially if you're inexperienced, but once you get your mind in the right place, it's not that hard to get through feelings if nervousness and insecurity.


Most Helpful Girl

  • I don't know how guys do it. I get approached all the time like tons of girls and... I love being social but I couldn't imagine what it's like to have to really try at approaching someone.


Most Helpful Guy

  • There's no reason to get a woman alone to ask her out on a date. Assuming her friends are even paying attention to you, they will probably encourage her to say yes because, unlike most guys, you had the balls to ask her out in front of them and they will respect it. You're 28, not in middle school. We all know that men date women. Trying to hide from other people that you're interested just makes you look weak and weird. I've asked women out in front of other people before, and no one pointed fingers and starting singing "K-I-S-S-I-N-G, first comes love them comes marriage then comes baby in a baby carriage".

    Also, what you say doesn't matter anywhere near as much as how you say it. If you ask a woman out and you say "well umm hey umm I was umm thinking that umm sometime we umm if you wanna umm maybe hang out together", then yeah, she's gonna look at you funny because you're acting like a scared little boy. If you're confident and simply say "Hey I gotta run but it was nice to meet you, we should hangout this week, what evenings are you free?" then schedule a date, that's fine. She's not stupid, she knows you're asking her on a date, and asking confidently will dramatically increase how often women say yes. Just use whatever words are normal for you, don't need to be formal about it.

    • Thank you. Some of your stuff should've been in the mytake. Definitely a different perspective with the group being ok to ask out in front of... but also consider his guide was written for a certain sort of person, the more shy kind of guy. We just can't feel confident in that situation and then fail your second point miserably.


Join the discussion



What Girls Said 1

  • Thanks for sharing. I'm a girl that is in the same boat you were in high school. Dating and asking people out is always so needlessly complicated. My friends had been convinced this guy liked me, and I couldn't tell if he was "giving signs" or was just like that with everyone. It's best for everyone to just be straight up. It's obviously easier said than done, but I really liked this MyTake.


What Guys Said 11

  • "Getting her alone" was the tough one for me. I had met my girlfriend before but we'd reconnected over a year later at an evening class. The problem was, she gave her friend a ride to and from the class and the friend would just chatter away obliviously, so I could never get much in the way of one on one time, never mind actual privacy to ask her out.

    I ended up doing it via Facebook Messenger! A year and a half later and we are still crazy about each other!

  • Good take that addresses several issues/questions, but it is truly easier said than done.

    Taking the first step is nearly impossible for me, even being 29. There have been a few times when I would consider it, then the topic of their boyfriend comes out. (Never even implied dating or anything, merely if they would be worth getting to know back from previous conversations back in college.) For some reason, all the people I end up beginning to take the first step with (wanting to know more about, not even necessarily dating) with end up having a boyfriend or married.

    Now, it's almost like being impaled and each motion to take a step is painful, regardless of which way you go, so you just don't move at all. It's kind of a catch 22 in a way, a self-limiting mental spiral. (Not to mention what any other person may say/think about it) As each year goes on, the more intimidating it becomes, the less desire you have to try and move.

  • I get the feeling this is probably going to happen to me in university, unless I experience some dramatic lifestyle changes. Thanks for the warning :p

  • I think there will be a lot more " late bloomers " in the future , this is because people are too glued to their phones to actually even know how to interact personally anymore , social skills will go down the toilet as a result !!

  • This is useful. Clearly written with the people who need it most in mind. Well done to you good sir.

    I swear reading this is like picturing the perfect prep talk from a dating coach or something...

  • Lol bungee jumping, paragliding, picking up fight you know you will get beating and surviving air assault for month can actually be easier on heart :P

  • "If you ask, you pay."

    I just never ask, problem solved.

  • And if it induces a heart attack cause it's that's serious

  • Just ask her out? Meh, easier said than done :(

  • White Knight 101

  • Great take. As a late bloomer myself, this all rings too true.

    I couldn't agree more with the over analyzing and reading into things. I'm guilty of this myself at times. There's this girl I started seeing who is very attractive and I have a lot in common with.

    But once she revealed to me that she just got out of a 5 year relationship, I was worried about being a rebound even though I felt a strong connection. I would also worry that if she didn't respond to a snapchat or text that I said something stupid that caused her to lose interest.

    • On top of that, before we had our 2nd date last week, it had been 3 weeks since we saw each other and when I'd ask to hang out on the weekends, she'd be busy and not offer to reschedule. This made me wonder if I was coming off as overly interested.

      Then last week she hit me up to go to a movie and that took the edge off, but I had to relieve some stress and do things to make my mind off of it because I was too stressed on whether she liked me or not. This made me realize that it's best not to over analyze or project things from the past onto a person as that causes stress and takes the fun out of it.