21 Ways to Start a Conversation with a Guy You like ...


You’ve seen him on the morning train every day for the past few months, and he’s so fine!

Out of the corner of your eye, you think you’ve seen him looking at you, but you can’t tell for sure… the attraction is there, so how do you start an actual conversation?

Here are my top 21 ways to start a conversation with a guy you’re interested in, along with a success percentage and how much courage you’ll need, on a scale of one (shy girls!) to ten (so bold!).

1. Catch His Eye and Smile

Catch His Eye and Smile

Level of Success: 60%

Level of Courage Needed: 6 of 10

The next time you see that guy, catch his eye and smile, maintaining eye contact for about three seconds before looking away.

If at all possible, blush a little when you look away.

I can almost guarantee that if the guy is interested too, he’ll smile back and probably even approach.

If he doesn’t, make sure to catch his eye and smile one or two more times, each time a little longer.

Toss your hair a little, and flirt like mad.

Let HIM start the conversation!

Photo Credit: Alex Rozhenyuk

2. Ask to Borrow a Pen

Ask to Borrow a Pen

Level of Success: 50%

Level of Courage Needed: 7 of 10

Bring a crossword or even just your agenda, day planner, or notepad.2

Rifle through your handbag, then get up the courage to smile brilliantly and ask him if he has a pencil or a pen.

Chances are, he will, and will be more than happy to share with you.

Use it to write a quick note or fill in a word, then put your notebook away and return the pen, thanking him gracefully.

Say something like, “Thank you so much!

You’re such a lifesaver!” If he’s interested, he’ll use this as a segue to begin a more meaningful conversation.

If he just takes the pen back with a nonchalant, mumbled “No problem,” move on.2

He’s cute, but not at all clever.

Photo Credit: biffybeans

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