How To Ask Someone Out on a Date

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? 

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About 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

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Ty Wilson
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Ty Wilson

I no longer make my “romantic intentions” known, because it’s taken the wrong way. I’ve been asked to come over and “chill” at 11pm, texted at 4:30 am and asked to meet at a hotel room less than 24 hours after meeting someone. No date, nothing that is suitable behavior from a gentleman. Pass.

Francesca Hogi
Guest
Francesca Hogi

I hear you, Ty. Sounds like those guys are not worthy of your attention. Obviously I don’t know how you’ve made your intentions known, but have you directly asked someone to get a cup of coffee or a drink?

Ty
Guest
Ty

Yes I have. Guess I should have asked for a room key, huh? LOL

guest
Guest
guest

I appreciate directness from a guy when asking me out on a date. It takes a lot of courage to put yourself out there, as I have done myself a time or two. At the same time, if I know I’m not attracted to a guy (physically or mentally), I won’t say yes and give him false hope. So I reciprocate their honesty and directness, even if my response is unfavorable. Moreover, I appreciate guys who have done the same for me and not gone on a “pity date.” I hope that guys (and females too) won’t let rejection deter… Read more »

Francesca Hogi
Guest
Francesca Hogi

I totally agree, a “pity date” is never a good idea. What I mean is that I find directness (again, in a RESPECTFUL way) very attractive. And I find that even if I’m not instantly attracted to a person, so long as I find him reasonably attractive, there’s always a chance attraction can grow.

Bobbi
Guest
Bobbi

I really enjoy asking a man out on a date. Lord knows if I will ever see the person again so why not just go for it, right? I have been turned down before and I was not in one bit “hurt” or said to my self “I will never do that again”. I also enjoy being asked out respectfully but asking a man out has always been a high point in my dating quest. #BeGreat

Francesca Hogi
Guest
Francesca Hogi

Get it, Bobbi!

Michelle Lynn Thompson
Guest
Michelle Lynn Thompson

You mean that little note with the check boxes won’t work?

Gillian Barrington
Guest
Gillian Barrington

Still don’t get it , is it to just walk up to a guy and ask him out ? It Seems almost desperate , I’ve always wondered what men think when they’re asked out. I’m kinda old fashioned in that regard but dam themes men sometimes can’t take a hint .

Gillian
Guest
Gillian

*these

Desiree M. Mondesir
Guest

I’m with you girl, totally old fashioned! 🙂

Francesca Hogi
Guest
Francesca Hogi

You might see it as desperation, but most men see it as confidence. There are plenty of desperate women out there who say yes to any man, put up with poor treatment from men and have never made the first move. You’re either desperate or you’re not. Asking a guy out is not the determining factor.

Desiree M. Mondesir
Guest

Personally, I’m not a fan of women asking men out. If someone else wants to do it, fine, but I won’t be doing it. I think if a man is truly interested, he’ll jump whatever hurdles are presently keeping me from him (bar me being in a relationship or, especially, married) and ask me out. Then again, I pretty much wear my emotions on my sleeve so (I feel like) it would be near impossible for him (whomever “he” is) to not know I was interested if I truly was. If I’m not interested, I don’t lead them on and… Read more »

Desiree M. Mondesir
Guest

I should also probably clarify that I don’t believe in recreational dating: dating just for the heck of it. I’ve always known since I was a girl that I could never date a lot of men. I get too attached; it’s just not something I’ve ever been interested in. And unless I get a good vibe about you from the get-go as far as marriage potential is concerned, I’m not interested.

And please, PLEASE don’t let your pick-up line begin with “The Lord told me…!” He didn’t. I promise. I heard Him. He said no. *walk(s) away*

Francesca Hogi
Guest
Francesca Hogi

Desiree, I hear you. But I think we have this idea that the only guy for us is the one who sees us across a crowded room, instantly knows you’re “the one” and will move heaven and earth to be with you. Just know that if you’re waiting for that, you might be missing out on good guys who maybe don’t have such a forward approach, the confidence, or even the immediate interest in you. Food for thought!

Desiree M. Mondesir
Guest

I’m not saying rejection isn’t a factor for men (and women); however, if a man wanted to attend the university of his choice, he’d apply. If he wanted a job or a promotion, he’d do what is necessary to obtain the desired position. If a man REALLY wants to ask me out, he is more than capable of applying that same drive to this situation, walking across the room, and asking me out. If he can’t do that, we don’t need to talk. My theory’s worked pretty darn well for me thus far. I can’t imagine why it should fail… Read more »

Francesca Hogi
Guest
Francesca Hogi

If it’s working for you, that’s great! I just encourage people to try something different if what they’ve been doing isn’t working for them.

It's me!
Guest
It's me!

I don’t believe in asking a man out because if you are a reasonably attractive woman, most men will more than likely just say yes just to try to get in your pants. I feel like if you at least wait for them to ask, it shows some sort of initiative and weeds out men who feel lukewarm about you or who are in it for one thing.

Francesca Hogi
Guest
Francesca Hogi

There are men who will do almost anything to get into a woman’s pants. In fact, some guys who are less of the “player” have a harder time asking out women, especially very attractive ones. Just some food for thought…

cocoafly
Guest
cocoafly

I need a man to be a man. I’ll approach a guy, flirt and drop all kinds of hints I’m interested. Now we should be asking a man out. I’m noticing a lot of advice coming from dating experts are for women to do more work. Teach these men to have guts and start asking out women.

Brian
Guest
Brian

Great read Fran! Growing up a country boy, I tend to sit more on the traditional side of things when it come to relationships, HOWEVER, I will say that I am extremely impressed by a woman who invites me out. I don’t see it as desperate at all! They don’t have to full on “Ask” me out, but a compliment, smile is usually everything I would need to realize that she may be interested. If it’s mutual, I’ll take it from there. To me, the whole “A man who FINDS….” is too often taken literally and used as an excuse… Read more »

navi28
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navi28

fSDI The Last years I was really, really lacking in $$ and debts were eating me from all angles!! That was Until i learned to generate money on the INTERNET. I visited surveymoneymaker point net, and started filling in surveys for cash, and surely i’ve been really more able to get around financialy! I’m very happy i did this!! IzAE

Bkchica
Guest
Bkchica

I’ve had a crush on my coworker for the amount of time that we started working together. We are friends, we do things for each other that my other friends think is not usual for coworkers to do for each other (I.e dog sit, borrow car, pick out paint colors, paint apt). On many occasions I wanted to let him know that I like him more than a friend (sheesh! I sound like I’m back in Junior high school!!), but I was never able to get those words out. He was single for awhile, but recently started dating someone. Now… Read more »

ElenaDariya1
Guest
ElenaDariya1

It is very difficult to meet the right one in this world
People are mostly liars and hide their real intention
I think i am a little bit lucky, because i met my hero on a dating site 
http://www.erisdating.com or http://www.angelreturn.com do not be hopeless, 
There are still nice and honest people who can give you the love you deserve
Life is short and it has no meaning without love…