How to Ask HIM Out!

Let’s be real ladies, it’s 2011. Women are CEOs, surgeons, and Hollywood film directors. With all of this career success, why is it that we can’t take charge of our own love lives?  Sure, it feels great to be pursued by your crush, but if he isn’t making the moves, why can’t you? Here’s how to turn the tables and ask him out.

Plan a Group Date. Obviously if you share friends, inviting him to a group outing is your easiest move. Having others around will help you to relax and make you feel like yourself. Find the right opportunities during the evening to get him alone. Maybe suggest you walk home together as you’re both heading downtown. Having a little private chat during or after your group date may encourage him to make the next move. Word of advice: Avoid inviting your Kim Kardashian look-alike friend. You want his eyes focused on yours.

Share Your Interests. Both foodies? Ask if he’d like to check out that new celeb chef restaurant with you one night after work. Root for the same home team?  Buy tickets for the next Mets game and let him know you’ve got an extra ticket to enjoy the sport, hot dogs, beer, and possible chemistry.

Suggest a Super Guy-Friendly Outing. Try to gauge what the guy you’ve set your sights on is into. As you’re chatting him up, ask him what he did over the weekend. Then, casually suggest something similar – whether it be going out for wings or to the batting cages – for the following Friday.

Ask If He’ll Be Your “Plus One.” Did you get an invite to a cool gallery opening or win free tickets to a concert? Ask him if he’d like to be your plus one! Avoid suggesting he join you at your sister’s wedding, since that plus one situation would freak most guys out.

If all else fails: Give Him Clues. Really can’t bring yourself to invite a dude out? Give him the green light to ask you. After flirting, say something like, “Have you heard about this new movie? I’ve been dying to see it.” It will give him the perfect opportunity to suggest you see it together – and because you’ve hinted at what you want to do, it takes some of the planning pressure off of him.

No matter what the approach is, remember that confidence in a woman is always sexy. And if that man can’t appreciate your approach, or is intimidated by your “forwardness,” he’s simply not the guy for you.

Sarah Shaker is an ex-soap opera producer, living, writing, and dating in the East Village. After launching Bright Lights, My City, a niche NYC lifestyle blog, she began working in community management and social media. Sarah is currently working for as the Regional Community Coordinator for, a hyperlocal website connecting neighbors to make their block a better place.

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  • Cindy

    Great tips! ( :

  • Herringbonesports

    Good stuff Sarah. Something tells me you have no trouble telling a guy whats on your mind in the ways of love. It doesnt matter, guy or girl, it’s always refreshing to be shown some mutual interest.

    Posts like these make me think that if I’m ever single again, I’m moving right back to NYC.

  • Skinose

    Great article!