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How To Ask Someone Out on a Date

The following guest post is from Francesca Hogi, a friend and fellow matchmaker. Be sure to read more about her company and follow her on twitter. 

It seems to me there are two types of people: those who are comfortable putting themselves out there romantically, and those who are not. I have always been in awe of women who have no problem just walking up to any guy who catches their eye, and I’ve taken for granted that it’s something that all guys figure out how to do sometime during adolescence. Now I know better.

Since becoming a matchmaker, I talk to people everyday about dating and relationships, even moreso than I used to (which was already a lot).  I am not surprised to hear most women express reluctance about asking men out.  But I am surprised by how many men who are smart, attractive and generally appealing are reluctant to be direct with women they’re interested in. As a result, they either resort to stealth (and usually ineffective) tactics to get a woman’s attention. The same goes for women. It might be really, really uncomfortable for you to ask someone out. You are not alone (in that fear). But you are alone (as in single), so it’s time to fake it ‘til you make it. Why should those other people have all the fun? 

1) Feeling rejected won’t kill you. REALLY. I promise.

This is all of our biggest fear. There’s not a person on the planet who says, “I really like this girl, I hope she tells me to F off when I ask her out.”  And there’s not a person on this planet who hasn’t experienced feeling rejected. But look at it this way: if this person isn’t available (for whatever reason), or interested (for whatever reason – don’t assume you know what that is – they might think your nose, which you hate, is really cute but they’re still in love with their ex), you’ve been freed up to find someone else who is available.  Besides, if a person is rude or dismissive in response to a respectful, direct advance, you’ve dodged a bullet!

 2) Don’t “date bomb”.

Not too long ago, I had a guy ask me out on a date. Only I didn’t know it was a date.  He was someone a mutual friend had connected me to via email regarding a business matter almost a year prior. He and I had exchanged a few emails and had one phone conversation, all in a totally professional context.  Several months later, he emails me out of the blue asking if I was free to get together to talk.  I agreed, thinking it was business-related.  After all, I had no idea what he looked like or anything about him personally.  It wasn’t until after we got together and he clearly had nothing of a business nature to discuss and described his ideal woman as someone who matched my physical description, did I realize I was on a date.  It would have been nice to get a heads-up of what his intentions were!  He quickly jumped into date mode and I wasn’t interested, nor did I appreciate being date bombed.

3) Don’t assume she/he knows you’re interested.

In an effort to protect our egos, it is sometimes safer to befriend the object of our affection than be upfront about your feelings.  It’s great to get to know each other as friends prior to dating, but be careful not to be so buddy-buddy that the other person assumes you’re definitely not interested.  It might be obvious to you, it might even be obvious to an outside observer.  But it might be lost on the person you actually like. The whole reason you’re taking this approach is because it isn’t obvious.  See how that might backfire?

4) Bite the bullet.

I am personally so appreciative when a guy is direct with me and just plain asks me out on a date.  Usually, I give him so much credit for his directness that I will say yes for that reason alone, provided he is respectful and reasonably attractive. These days, it’s so easy to hide behind Facebook “likes” and indirect come-ons, you distinguish yourself by being upfront.  Same goes for women – guys love being asked out and it doesn’t happen everyday, even for the most eligible bachelors (sexual come-ons don’t count). If the possibility of hearing a no makes you cringe, re-read #1 above.

How about you? Are you good about making your romantic intentions known? Have you ever come right out and asked someone out on a date? 

Paul C. Brunson

Mentor, Entrepreneur, & Television Host. My goal is to help you live your best life. I’m the world’s most influential matchmaker, founded and exited three businesses, host two television shows, spent nearly a decade working directly for a billionaire, and share my experiences by mentoring through Knowledge Share