How to Ask Someone Out Whom You Have Had a Crush on for Years

Ask out your crush in a comfortable setting.

Every time that he comes around, butterflies appear in your stomach, and your speech becomes impaired. You imagine that you and he would make the perfect couple and be the envy of your friends. One problem, though, is that you've yet to fess up about your feelings for him or to even go on a first real date. Many marriages begin with a foundation of friendship, so knowing him for years may make it easier to read him and to see if he might reciprocate your feelings. But you'll have to ask him out before your relationship can begin.

Instructions

1. Plan for the encounter psychologically. Put everything in perspective, such as realizing that the worst thing that she could say is "No," but if she agrees, your courage could result in a wonderful relationship. Even if you have been friends for years and she declines, your friendship will recover and you can move on to someone who is more interested in you and deserves you.

2. Rehearse what you will say. Look at yourself in the mirror, and say the words you plan to say when you ask him out. Try different versions until you have the speech that sounds the most like you.

3. Decide where you will ask her to go with you. Avoid high-pressure situations, such as expensive trips, events or restaurants. A coffee shop, ice cream shop or bistro provides a low-pressure and casual place for a first date.

4. Talk to him in the right setting. This should be a private place where he feels comfortable, such as his home or a hangout spot. Don't talk to him in front of other friends because he may be embarrassed or agree to a date just to avoid embarrassing you. This will give you a false impression on any feelings he has for you.

5. Send flirty messages, especially if you are the woman. Traditionally, men are the ones to play the aggressive role, and it's the woman's job to show she is interested. Put your arm around her or brush against her hand if you are the guy. If she rebukes you or shrugs away, she may not be interested and you may want to stop there.

6. Downplay your feelings when you talk to her. Do not begin your request for a date by gushing about how long you've loved her. This will probably cause her uneasiness, and she will likely decline.

7. Tell him your intentions. Say that you want to find out if you two have a connection beyond friendship, and you would like to go out with him. Specify where you plan to go.

8. Maintain eye contact and smile. Eye contact is a nonverbal sign that you are interested in what she has to say and that you're sincere. A smile often makes the other person relax.

9. Wait for a response. Don't keep rambling on after you've asked for the date. Let him accept or decline, and accept his answer gracefully.

References

• Teen Vogue; Should I Ask My Crush Out?; Rachel Simmons; April 2011
• The Art of Manliness; Stop Hanging Out With Women and Start Dating Them; Brett and Kate McKay; January 2008
• Ask Her Out: How to Ask for a Date Without Pressuring Her
• Playing Love Games: How to Ask a Girl Out
• The Tartan; How to Ask Your Crush Out; Alex Yuschik; February 2009