Dating a Woman Who’s Way Out of Your League

Florence Williamson
3 min readJul 20, 2022


First of all, leagues are subjective.

But let’s face it. Some women have beauty and wit that can knock your confidence down. You may be in love with one right now. Maybe she looks like a Victoria’s Secret angel; or so eloquent that you feel inferior; or so accomplished she makes you look like a wimp.

Still — you like her and you want to pursue her. You might think it’s impossible to get her, but it’s not. You just need the right moves and attitude to woo Miss Intimidating.

1. Put her looks aside.

Are you only after her because of her beauty? If your reasons are this shallow, then don’t waste your time or her’s. You might only end up resenting her because she’s incredible and you think you’re not.

But if you see a relationship with her beyond her looks, money, or popularity, then go pursue her.

2. Don’t fear rejection.

She may seem out of your league, but don’t assume she won’t date you. Give it a shot and make a move.

Gather up the courage to say hello. Shake off your nervousness and flash her a bright smile. Show her that you are genuinely interested in getting to know her.

You’ll never know. Instead of rejecting you, she might give you a chance.

3. Strike up a conversation.

Conversation eases rejection fears and lifts tension. Learn the things she loves to do, then see how you can relate to them.

And make the conversation a fun one. Give her a good time so she gets comfortable around you. It might also encourage her to open up.

Get to know her beyond her looks or money. Maybe you’ll discover great things that people fail to notice because they’re too focused on her external qualities.

3. Appreciate her.

Let’s say she enjoyed talking to you and finally, agreed on a date. Don’t waste your chance to make her feel appreciated.

On your date, be more than a gentleman. Don’t be a bad boy wannabe. Chances are, she’s had enough of those kinds of guys and just wants someone who’s genuinely nice.

Compliment her beyond looks. Maybe she loves writing poems but people overlook it because of her beauty. Read them and try giving genuine comments. Hear her speak about the passion and dreams she wants to accomplish.

Make her feel special and beautiful beyond what she is known for.

4. Be honest.

Yes, she’s intimidating. And that drives you to want to impress her more. Feel free to do and say whatever you can to get her attention, but never lie. Never lie about non-existent achievements, talents, and stories. Don’t woo her with gifts you can barely afford.

Show your true self instead. Share the real you, the talents you are proud of, and the accomplishments you worked hard for. Tell her about the dreams you’re working on.

Simply, put the focus on your strengths. Not on the things you wished you had.

That way, she’ll realize that it is enough to be with a man like you. Someone honest and has substance.