Now Reading
How to Ask Someone Out

How to Ask Someone Out

When I was in high school and college, the easiest way to ask a someone out was Instant Message. If you wanted to get to know a girl or guy without risking rejection, you somehow got their screen name then flirted relentlessly through cryptic Instant Messages.

It’s no secret that texting is the new norm. The amount of effort and the gall it takes to stand face to face and ask someone out is slowly fading.

Young people no longer have the nervous coming-of-age experience when they stare into a someone else’s eyes, heart pounding with fear of rejection, and ask them out for the first time. A 2012 study reported that 67 percent of high school students hide behind a screen and shoot a text to ask their date to prom.

But it’s not just high school students. As USA Today recently reported, approximately 38 percent of 21-26 year olds and 36 percent of 27-34 year olds schedule dates over text.


So what? It’s just modern communication, right?

Your dating strategy is your decision, but may I suggest that there is a better way to find a man or woman worth committing to? If you’re wanting more from your dating life and have desire to grow in character, integrity and respect—I’m here to help.

Before we begin, I feel we need to clear something up: A group hangout is not a date. I repeat, a group hangout is not a date. It is a great way to get to know each other, but it sure isn’t a date.

One other thing: in today’s culture, it’s generally the guy who does the asking. There are a lot of different views on whether or not guys taking the lead is a moral imperative, and that conversation is beyond the purview of this article. That said, this advice is useful for whoever takes the initiative.

The steps to asking someone out:

1. Start by getting a number, i.e. don’t ask their friends. Don’t text, tweet, Facebook, email, comment on their blog or chat them.

2. Figure out where you’d like to take them, on what day and what time before you ask. It’s your job to have a plan if you’re doing the asking.

3. Call at least four days in advance of when you’d like to see them, and set the time at an hour that doesn’t come across as a booty call (like, say, 11 p.m.)

4. Take them to a public place for your first date. Don’t go on a long drive into the middle of nowhere for a picnic. That’s how horror movies start.

5. Pick a place that is unique and provides a good atmosphere for listening. Yes, you heard correctly: listen.

6. Make them feel comfortable. Some examples of topics that are off limits: politics, past relationships, racial comments, kids, marriage plans, your fraternity if you’ve been out of college for more than three months.

7. Ask questions. Ask what they’re interested in, what they love (or don’t love) about their job. Keep the conversation light-hearted.

8. Make them laugh. I cannot tell you how important this is. Make fun of yourself, tell a joke, share a funny story—anything to get them to laugh.

9. Do not, under any circumstances, divulge the following:

– Your childhood secrets
– Your family drama
– Your history with foot fungus
– Your psycho ex-girlfriend/boyfriend
– How much you hate your boss (don’t be a complainer)
– Your 3 a.m. donut-eating habits
– Your sexual history
– Your daily phone call with your mom
– Your video game domination

Then pull out your wallet and pay the bill. You asked them out, didn’t you? Don’t split the bill. Don’t let them pay the tip.

Did it go well? Great. Call within three days and ask them out again. Repeat steps above.


Now, if it didn’t go great and you decide that you don’t want to keep dating them, be straightforward. Don’t disappear into thin air, don’t keep texting, don’t make out, don’t hope they get the hint without you having to tell them.

Tell them with audible words that you won’t be calling anymore because you aren’t interested in a romantic relationship. It might sting a little, but it’s better than leading them on for months or sending them unclear texts they’ll have to decipher in hundreds of discussions with their friends. Be an adult and don’t hide behind vague intentions and confusing relationships, keeping in mind that Real Men Don’t Text.

Remember you are not asking them to marry you. It’s just coffee, or a drink or dinner. It’s not a marriage proposal. You are not locked into a long-term contract. But the purpose of dating is to figure out what you like, enjoy time with the other person and learn the skills necessary to develop healthy relationships. If you can’t muster up the courage to call, then you aren’t ready to date.

View Comments (9)

Leave a Reply

© 2023 RELEVANT Media Group, Inc. All Rights Reserved.

Scroll To Top

You’re reading our ad-supported experience

For our premium ad-free experience, including exclusive podcasts, issues and more, subscribe to

Plans start as low as $2.50/mo