How to Ask a Guy Out Even When You’re Totally Awkward

Dating 101
22 Apr 2023
11 min read
How to Ask a Guy Out on a Date

You like him. You really like him. You’d love to ask him out, but you’re feeling a bit shy. Every time you try to work up the courage to ask a guy out over text or in person, you just can’t do it. What’s going on?

If you want to learn how to ask a guy out, you’re not alone. So many women and men both struggle with this step. Sadly, that means missing out on spending time with someone really special.

Fortunately, you can overcome this hang up. It’s true! Anyone can learn how to ask a guy out. Here are some easy, low-pressure tips to help you out.

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What Makes This So Hard?

Why is it so hard to ask a person out? There are a few reasons for this. The first is our socialization. You would think that the notion that only guys ask girls out would have died a few generations ago, but it hasn’t. At least it hasn’t gone away completely. Men are perceived as being the ones who pursue, and women are still seen as the ones who should wait until they are noticed.

As a result, it can feel quite awkward to ask a guy out. There’s also the fear of rejection. Finally, women often don’t have much practice when it comes to asking a guy out for a fun time.

Why Can Some Women Ask in Such a Natural Way?

Then again, there are some women who seem to know exactly how to ask a guy out. They get everything right from body language to eye contact to coming up with the perfect opening line.

How do they do it? First, they relax and play it cool. They know that it’s just a date. The worst thing they will hear is no. So, they don’t worry about blurting out a terrible pickup line. They treat it as a casual conversation, not some nerve-wracking audition for a date. This light-hearted approach puts them at ease as well as the guy they are dating.

“Your real work in life is to fill yourself ’til your cup runneth over so that you’re never grasping and needy, clamoring and insecure.”

Oprah Winfrey

8 Tips for Asking Him Out

It’s great that other people know how to ask a guy out, but you certainly don’t feel calm or about any of this. The idea of blowing it with the right guy and getting rejected sounds absolutely awful to you.

Unfortunately, we can’t remove the emotional risk completely. We also can’t guarantee that you won’t feel awkward. However, we can offer up these great tips for asking someone who is boyfriend material to spend some face-to-face time with you.

1. Put It in Perspective

Most guys are flattered when you ask them out. They think it’s sexy when you make the first move. Sure, there are a few jerks who might make you feel bad, and that sucks. That said, better to learn now who is a jerk than to suffer through a first date with somebody who is simply awful. Yes, it’s possible that he will say no, but don’t let that lead you to avoid putting yourself out there. Instead, treat it as a learning experience and some good practice for the next time you ask a guy to spend time with you romantically.

Related reading: When No Response is a Response – How to Know

2. Find Your Common Interests

It is so much easier to ask a guy out when you have a common interest. Forget about the standard boilerplate outing. Instead, ask him to a really cool event that you’ll both enjoy. For example, offer up an extra ticket to a sporting event or beer fest. Use your imagination and create a date that involves both of your mutual interests. He’s more likely to say yes if you have something fun planned, and you’ll both have a much better time!

Group date is a great answer to a question how to ask a guy out

3. Hedge Your Bets With a Group Date

A group date creates a low-pressure situation for everybody. You can go out with your friend circle, and have a great time. You can even use actual date ideas to invent something interesting and easy-going. At the end of the night, you may conclude you are just friends, or decide to ditch the friend talk for a bit of romance. Either way, it’s no big deal if things don’t go perfectly.

4. Use Your Body Language

You’re going to feel awkward doing this, but try rehearsing a bit before you attempt to ask him out. If possible, get your best friend to play the role of “the guy”. Have them pay close attention to your body language. Practice your smile and confident head nod. Your friend will give you some great feedback, and it will be good for a few laughs. The most important thing is that you will be better able to come off as fun and flirtatious when you ask the guy out. While you’re at it, you can work on some great pickup lines.

Related reading: Is He a Body Language Guy? How to Read The Subtle Signs

5. Try Asking Him on Not Quite a Date

There is nothing wrong with testing the waters. If you don’t feel fully confident asking a guy out for a romantic evening, go with something casual and friendly. He may be more likely to say yes if he is feeling ambivalent. So, try a coffee shop date instead of a romantic evening at the priciest restaurant in town.

Dates that involve activities are also a better idea if you don’t want to come on too strong. Play the long game and ask him to come out to a trivia night or to that awesome vintage arcade in your town. You will be able to talk and have fun during your date, and nudge things towards something a bit more romantic.

Ask your mutual friends for mutual interests

6. Get Insights From Mutual Friends

Do you have friends in common? Hit them up for a few tips. Good friends will let you know what he likes, and will help you come up with a great idea for a date. They may even be able to let you know if the guy is mutually interested too. Remember to ask if he has a girlfriend. You want to respect that existing relationship, and save yourself from an awkward conversation.

7. Always Be Paying Attention

You want to come up with a great strategy for asking this guy out. The best way to do that is to be on the alert. Pay attention to his sense of humor. Learn what he likes to do. Get an idea of his overall vibe. Use this information to plan a great date, and your approach to asking him out.

8. Make the First One a Casual Date

Asking a guy out is high-pressure enough. If your plan fails, you don’t want to be disappointed after planning some elaborate night. This is not the time to invest in two tickets to an expensive concert. Instead, send a text message inviting him out for some casual fun.

However, you shouldn’t be too casual. Be sure to have a specific activity in mind. You want him to feel special, not like an afterthought.

Keep an eye contact to feel confident and see everything

5 Cringeworthy Mistakes to Avoid When You Ask a Guy Out

Mostly, awkwardness comes when you do something cringy. To make things comfortable for both of you, check out these mistakes to avoid any time you ask a guy out.

1. You Make Him Seem Like a Jerk Off the Bat

You may be tempted to save your ego by making negative assumptions about his interest in you.

You might say, “I know you probably don’t feel the same way about me,” or “You probably wouldn’t want to date someone like me.” 

Don’t do this. First, you want him to feel excited about dating you, not guilty. Also, it’s simply unfair. He should be able to say no to a date without being made to feel or look like a jerk. Besides, you just end up sounding desperate. Instead, ask the guy in an open and friendly manner. Then, make it safe for him to tell you if he is interested or not.

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2. You Neg Him or Engage in Reverse Psychology

Negging and psychological games will cause a guy to lose interest quickly. Sure, there are all sorts of blogs on hookup culture that recommend these techniques, but in real life these techniques almost always flop. When they do work, you don’t end up with the perfect guy. Instead, you get somebody who is needy and easy to manipulate. Is that what you want out of your next boyfriend?

3. You Engage in Pick Me Behavior or Feigned Helplessness

Has a guy ever told you that you fawn too much? Do you have trouble hanging on to women friends? Have you been socialized to believe that a cute way interact with gays is to pretend to be helpless or childish? Do you think that the way to get the undivided attention of guys is to compete with other women?

Here is some advice that will help you with your relationships with guys and other women. Stop doing that. A good guy won’t find that kind of behavior attractive. Women will see you as untrustworthy. Girl, you can do better than that! Work on becoming an interesting, engaging person. Then, you won’t need to put on a fake persona or denigrate any other girl to get what you want.

4. You Take Forever to Get to The Point

We get it. You’re nervous. Few people can just ask a guy out without feeling a bit anxious. But, when you ramble on without getting to the point, you just make things worse. The chance that you will say something awkward increases dramatically. The person you are asking may go from being interested to just thinking you are weird.

Asking a guy out is like giving an elevator pitch. Plan what you are going to say, and get it done with! This is even true for asking a guy out over text. Don’t send multiple messages, especially if you are text texting as opposed to messenger. Instead, keep the conversation short and just ask the guy out!

5. You Conspire With Your Friends

Here are some things that are fine to do before talking to a guy and asking him out for the first time:

  • Get some advice from your best girl friend
  • Practice some great opening lines
  • Commiserate with your friends over how difficult this is
  • Ask friends if you share common interests with the guy you like

Here are some not so great things to do:

  • Have a friend do the talking and ask him for you
  • Bring friends with you while you ask
  • Conspire with friends to create some elaborate date proposal

A good guy will support your friendships, but he doesn’t want them in on every conversation you have. Also, if you are afraid to approach him alone to share your feelings, that’s likely to creep him out a bit. So use your friends for support, not as something to hide behind. Finally, those cutesy asks are a quick way to get him to lose interest in any sort of relationship with you.

Surviving Rejection: Part of Learning How to Ask a Guy Out

There is no way to ask a guy out without risking rejection. That’s just part of it. Here are a few more tips on getting through this experience with your feelings intact:

  • Accept no as an answer
  • Ask why if that’s appropriate – then respect the answer he gives
  • Don’t beg, whine, or negotiate
  • Stay in control of your feelings – don’t cry or lash out

Try to find out if his refusal is based on him not wanting a relationship with you, or a logistical issue. For example, see if a specific day or a specific time would work better for him.

Whatever happens, don’t be afraid to try again with somebody else. There is sure to be a person out there to connect with you.

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Don’t Feel Awkward: Go For It!

You want to go on a date with a great guy. That isn’t going to happen unless you get over it and just ask. So, walk over there and talk to him! You can start by composing a short message and hitting send.

Remember: there is no perfect way to ask him out. The worst mistake you can make is to not mention you are interested at all. Besides, if you hit it off with him, you will probably look back and laugh at how nervous you felt.

Dating Tips Author
Shelly Standford
After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!

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