20+ Awesome Ways To Ask A Guy Out

With these suggestions, you will always feel confident when approaching a guy to ask him out.

You admire his charm and charisma; his appearance, stride, and demeanor captivate you. You desire to be in his company but are unsure how to make the first move. It may seem daunting, but rest assured, we can help you out.

Below are some creative and engaging ways to ask a guy out. While it may initially seem daunting, these suggestions are straightforward and efficient. Don’t let the fear of rejection or jeopardizing a friendship deter you from pursuing someone you have feelings for. Exude confidence as you elevate your hidden or evident admiration to a new level.

Awesome Ways To Ask A Guy Out

At first, it may appear challenging, but inviting a guy out is relatively straightforward. Here are some effective methods to help you with this.

A single mother who prefers to remain anonymous shares her experience of asking men out on dates after participating in a challenge introduced by a Facebook group called ‘September is Take A Guy Out On A Date Month.’ She mentions that despite the lengthy name of the challenge, she and her friends decided to give it a try last year and enjoyed it so much that they have repeated it twice since then. They are planning to organize another one at the end of the month. Although some have faced rejection and approaching someone for a casual outing can still be intimidating, the overall feedback from everyone involved has been positive.

Although challenging, our dates have been delightful and well worth it. The simplicity of our dates allowed us to enjoy each other’s company. Although we missed the target date of September and started in October instead, we could bounce back from rejections and ask someone else out. There was a concern that we might approach someone uninterested in dating women, but fortunately, that did not happen. Through these dates, we got to know our partners and the others involved on a deeper level than we anticipated. It was a diverse group of people who may have yet to cross paths under different circumstances, which added to the fun.

If you need advice on asking a guy, here are some practical tips to simplify it.

1. Send naive texts

For some people, asking someone in person can be intimidating, so consider sending a sweet text instead. You could try sending him mysterious or ambiguous messages like:
I have developed feelings for someone with whom you are familiar.
We must have been together in the past because we got along so well.
Shall we go out…oh, forget it.
You know I enjoy yo…um…yogurt?”

2. Send sweet messages

To ignite rogue, you could attempt a playful gesture, such as discreetly sticking post-it notes on his desk or in a place where only he will notice. Write messages like ‘I like you’ or ‘You’re looking good, my handsome’ or any other message you wish to convey. Afterward, send him a text letting him know that you left something for him to read. This sweet gesture may leave him feeling excited and impressed.

3. Compose a gentle poem

Express your strong emotions for the guy through poetry. It doesn’t have to be perfect; even a simple verse will suffice. End the poem by inviting him to respond via email or meet you at a designated place and time.

4. Seek his assistance

One way to ask him out is by requesting assistance with something you believe he would be good at. Afterward, go for coffee or ask him to join you for a meal at a restaurant you like. It’s important not to appear overly eager for a date.

5. Inform him that you are feeling hungry

If you have a good relationship with him, approach him and tell him you’re hungry. Mention that you dislike dining alone or want to check out a new restaurant. If he agrees to join you, consider it a date. Engage in conversation and learn more about him before confessing your feelings.

6. Ask for a gift

Playfully request a gift from him when he greets you on a special occasion like a holiday or your birthday. Initially, he may be surprised, but if he inquires about your desire, express your wish to have a date with him as his partner.

7. Provide him with an additional ticket

Discover a game or event he is interested in and tell him you have an additional ticket. You have successfully arranged a date if he decides to go with you.

8. Spend time casually together

If you suspect the guy is interested in you, suggest spending time together. You can propose meeting at a restaurant or a cafe to chat. When you sense an opportunity, express your feelings towards him.

9. Experiment with using a pick-up line

Only some people rely on pick-up lines, so trying one on him could catch him off guard. Even if the line is cheesy, the goal is to get him to smile and agree to go out with you.

10. Discover shared interests

The person you are interested in may have a passion for guitars or books. Similar interests can lead to engaging conversations. By connecting over shared interests, you can capture his attention and create a bond with him before expressing your feelings.

11. Have a sense of humor

You might have a close friendship with him and frequently spend time together. Consider expressing your emotions in a lighthearted and humorous manner. If he responds thoughtfully, take advantage of the opportunity. If not, treat it as a joke to prevent discomfort between you.

12. Engage in playful banter with him

To flirt with him, you can inquire about his relationship status by asking questions like “Do you currently have a girlfriend?” or “Are you looking for a girlfriend?” Pay close attention to his answer to assess the situation accurately. If he responds positively, you can proceed by expressing your feelings and letting him know you are interested in him.

13. Have a friend introduce you

If the person is not easily accessible, consider contacting mutual acquaintances for help. Ask them to facilitate an introduction between you and him. Before meeting him, inquire about his hobbies, preferences, and aversions.

14. Engage in an entertaining activity

Determine his feelings towards you by posing a series of questions to him in the form of a game. Begin with lighthearted inquiries before inquiring about his preferred type of partner. If his responses appear favorable, consider inviting him on a date.

15. Invite a friend to act as your support or companion

If you cannot talk to him first, ask a friend to help. Your close friend might be bold, approach the guy, and act as a matchmaker. She can suggest that it would be nice for both of you to talk and get to know each other.

16. Leave a message inside his book or CD

Borrow a book or CD from him and insert a note expressing your emotions towards him when you give it back. Let him know it’s fine if he doesn’t reciprocate your feelings.

17. Find out more about his passion

Discover his main interests and use them as an opportunity to initiate a conversation. For example, consider asking him for guitar lessons if he is passionate about guitars. Accepting his offer to teach you can create more opportunities to spend time with him before expressing your emotions.

18. Request to go on a group outing instead of a one-on-one date

If you feel uneasy about asking him for a one-on-one date, consider organizing a group outing instead. You could also get invited to a group event he will attend. Once you’re all together, please try to start a conversation and stay close to him. It’s easier to talk to him when friends surround you; if he doesn’t seem interested, you can smoothly transition to chatting with other friends.

19. Get him to propose to you by tricking him

Men enjoy being the hero and helping others. Therefore, if you mention to a guy that you’ve been wanting to check out a new bowling alley or restaurant but need someone to go with, there’s a good chance he may offer to accompany you.

20. Provide him with a way out

If you notice someone in your group feeling bored or disinterested, suggest going to a more enjoyable party or location. Once outside, lead them to a peaceful spot and express your desire to spend one-on-one time with them.

21. Be honest and direct

Sometimes, being upfront can be effective. If you have communicated with this person for some time and believe they may have feelings for you but are hesitant to move, consider taking the initiative and asking them out yourself. They could be pleasantly surprised by your boldness and may be enthusiastic about accepting your invitation.

Common Errors to Steer Clear of When Proposing to a Guy

Asking a man on a date requires courage and can empower you, but having the right attitude and plan is essential. By preventing typical errors, you can improve the likelihood of receiving a favorable response and arranging a meeting.

• Make it simple; complicating things too much can lead to unnecessary stress.
• Observe his body language and pay attention to his reactions during conversations to gauge his level of interest.
• Clarify your intentions to avoid confusion between a casual hangout and a romantic date.
• The best approach would be to inquire in a private or calm setting rather than a public place. This would allow him to respond without feeling any stress from others watching.
• Choose a date suggestion that will bring pleasure to both of you.
• Staying true to yourself strengthens a relationship. Avoid altering your true self to maintain a genuine connection.
• Please don’t take it personally if he says he’s not interested.

Asking a guy out can be challenging, but staying composed is essential. It’s natural to feel anxious while waiting for his response or before approaching him, but it’s necessary to maintain a calm and collected attitude. The tips on how to ask a guy out can be helpful in this situation. Approach him confidently, suggest hanging out together casually, or enlisting a friend to help play matchmaker for you. If things don’t go according to plan, don’t be disheartened. Brush off any setbacks and continue searching for the right person.