Go On, Talk To Him

From an anonymous reader: So somehow, I always manage to get totally embarrassed and confused while approaching a guy. I think it is because I get really nervous. Even the thought of approaching a guy makes me tingly. Just like last time, I was hanging out with my friends at the bar and after all the ‘Go do it’ and ‘Go on!’ from my friends, I finally gathered the courage to go up to him and break the ice. My icebreaker? “The clouds look good today don’t they?” Now this was really embarrassing, because as soon as I said that, the weird look on the guy’s face reminded me that we were indoors and he couldn’t really see the clouds (duh). I just turned around and sat back down with my friends with sweaty palms and no courage to even look at that guy again.

So now there is this guy I see on the train a lot, we have shared a lot of ‘slow-motion-dramatic’ eye contacts. This one time he approached me, I was so nervous I could feel sweat drops running down my back, he threw a “How you doin’ today?” at me, but I simply choked and could only muster up the courage to smile like an idiot. What do I do? I don’t want to use cheesy pickup lines that will end up making me look slutty. Still, I still need to engage that guy in a conversation or I won’t be able to forgive myself. I even wake up in the middle of the night thinking about that guy. It has come to the point where I really hate myself for not being able to flirt like a normal person. Help me.

Is It Normal For Women To Approach Men?

I have been with girls from around the world and according to my experiences; the case of the anonymous shy girl is not that uncommon in the dating world. The world we live in today has changed a lot. In the olden days, a woman would neither bear the burden to start a conversation nor would she be expected to break the ice. Now, it is not just opposite for women to approach men, but it has gradually become a norm. Wishing to approach attractive men (the ones you find attractive) is as natural for women as it is for men to approach women. However, not every person has that natural charisma, or the confidence, to step up and ask out the man of their dreams. So how do you do it?

Be Yourself!

The first and foremost thing you should consider doing and it would add to your confidence is, be yourself. Avoid putting on extra makeup, or trying too hard to look good. This often hinders a woman’s approach towards men, as they are already concerned if the dress they forcibly squeezed into is showing their curves right. Being yourself naturally boosts your confidence and lessens the risks of you stuttering or having to go through the walk of shame after a failed attempt. I would prefer a girl coming up to me and being herself, rather than a girl with loads of makeup and a dress that does nothing but hides her own personality.

Pickup Lines For A Guy You See Yourself Going A Long Way With

Pickup lines or conversation starters also largely depend on where you are, the “clouds looking good” at a bar was a major fail. It would have totally worked in an outdoor situation though. The lesson here is to use the right line in the right setting.

Of course the simple “How you doing?” and “Where do you work?”, “What do you do?” questions would definitely give you a point to start but I doubt if they would get you some action. However, if you are looking for a serious and mature relationship, starting off with the “have we met somewhere before?”, “How boring is this?”, “Can you help me with these bags?” or a simple “Can I sit with you?” would work great. Guys like having their share of attention and being praised, don’t be afraid to make a few comments which put your feelings out in front. Being a guy, who is well-versed in the ins and outs of dating, I can assure you that approaching the guy you like upfront, is the best action plan since it shows you are confident and seriously interested.

Party, Bar, Drinks – Getting A Little Tipsy And Just NEED That Guy?

Ok so you are at the bar with a couple of friends, it is a weekend, you have your best dress on and you notice this absolute stud fiddling with his glass on a table nearby. You are lost in that staring-spree when all of a sudden you realize, he’s staring at you too.

The eye-game goes on for a while and you feel like going up to him and making him yours. You just had another few rounds and you can’t resist that stunner no more. What to do? This is where most women think that backing off is the best strategy, when it isn’t. Such situations don’t come easy, to be exact, such easy situations, where you can act dumb/cheesy/funny/dirty (because you are drunk, Duh!).

Just walk up to him, with one thing in mind, you are going to have a real connection with him and a lot of fun in the process. (keep it low on the booze if you think you are going to hit on a guy) and just throw some of these at him:

(Disclaimer: These lines are not for the ladies who are looking for long-term relationships.)

(Disclaimer 2: Use your best coy smile and semi-sarcastic tone of voice for best results.)

  • The Broken Bed

“Hey my bed is broken, can I sleep in yours?”

  • The Cute Sarcasm

“I know somebody who likes you a lot and if I wasn’t this shy, I would tell you who it is”

  • Straight Up

“You are just the way I like my coffee, tall, dark, and strong”

  • The Santa Bomb

“Can I take a picture with you, so I can show Santa what I want for Christmas?”

  • Glued-Eyes

“There must be something wrong with my eyes cause I just can’t get them off you!”

  • Aren’t You The Guy

“Aren’t you the guy who’s supposed to buy me a drink?”

  • The I-Want-You

“So, what does it feel like to look so good?”

  • The Wake-Up Bomb

“Tomorrow when I wake up, I hope you’re the first thing I see!”

Remember, at a bar, most men you see are approachable. How you approach them and what you say will most probably determine the future of the relationship. Ladies looking for a short fling should go with one of the pickup lines I have mentioned in the article. In my experience, I have never seen a drunk guy refusing an offer from a slightly tipsy girl.

As for the shy anonymous girl looking to break the ice on the train, next time simply introduce yourself, smile, and let him continue the conversation. In your case, the guy is probably as nervous as you are so a disarming smile is the best course of action. You should not go for a pickup line, just use a simple ‘how do you do’, and it will work.

Talk soon,

Joshua Rose

P.S. If you enjoyed this article and want to read more like it, please leave me a nice comment in the sections down below.

Leave A Reply (3 comments so far)


  1. Paula
    4 years ago

    Thanks for the tips – much appreciated. I married at 20, stayed faithfully married for 30 years, and now am trying to screw up the courage to start over. But it’s been so long that I’m extremely nervous and can use all the help I can get. What worked in school to pick up guys isn’t going to work now that I’m 59 LOL


  2. Dolores
    4 years ago

    I enjoyed the samples you stated. Do you have any examples of how to start a conversation on a dating site.


  3. Terri
    4 years ago

    Cute pick up lines if you are tipsy and hope to get lucky. I don’t drink enough to do that though. Good ideas though.

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