You and your guy friend may enjoy spending time together, but you are on the hunt for something more. Learning his feelings about you can be difficult and can leave you feeling uncertain of how to proceed. While asking out anyone carries difficulties, there are ways to ask him out without creeping him out.

Asking for Dates

Though the two of you may already hang out often, adding a little flattery into your requests can go a long way in setting the stage for asking him out. Rather than asking if he is up for going bowling, you make a bolder statement. Try statements such as, "I definitely want to spend time with you tomorrow. Why don't you pick me up to go bowling?" suggests social and personality psychologist Jeremy Nicholson. You might also try saying, "How about I take you out on a date?" or "We're both single - let's go have fun."

Asking Him Out

If the friendship is new, take time to feel the situation out first. Increasingly spending time together is a necessity before taking the plunge and asking him to be your boyfriend. When you do have the conversation, you might start by bringing up all of the fun you have together, and the positives that each of you brings to the other person's life. You can then say to your guy friend, "I care about you, and I was wondering if you also thought about dating me."

The Aftermath

It is quite possible that your guy friend shares your feelings, as opposite-sex friendships often involve attraction from both sides, according to the Two of Us article, "Opposite Sex Friendships." If the attraction is not mutual, you can say, "I must have misread things. I hope we can still keep being friends, because I still enjoy your company." If one or both of you need time apart from the friendship to reassess things, remember that relationships constantly shift and change and this may only be a temporary growing pain in your friendship.

Possible Concerns

If your guy friend routinely talks about his crushes at school with you or tells you that he thinks of you as a sister, keeping your feelings to yourself may be for the best, according to the TwoofUs.org article, "Dating a Friend: When is it a Good Idea?" If your friend seems uncomfortable with your advances, or tells you that he is not interested in dating anyone, it may also be wise to take his words at face value. Not every love interest will pan out, but fortunately, you will have a friend by your side as you seek out your next crush.