Advice on How to Ask a Friend Out

Contributor: Lori Gorshow
group of friends hanging out

Do you need some advice on how to ask a friend out? Let our dating coach give you some tips!

Wondering How to Ask a Friend Out?

The fear in asking a friend out is that the friendship will suffer, either because you try a relationship and it fails or because your friend feels odd about getting asked out. Dating coach Lori Gorshow cautions that you should take care to not blindside your friend with your feelings. "One of the problems with liking someone you've been friends with is that they may not be aware that your feelings have changed from 'just friends' to 'more than just friends'" said Gorshow. "This is because the same behaviors that would show you are interested in a particular guy are similar to the ones you show when you are comfortable and relaxed around a guy friend."

The Importance of Timing

"If there was a time when this guy liked you more than just a friend, you probably weren't aware, so he gave up," said Gorshow. "Likewise will be the case for you. However, with a little planning and some help from your friends, you can turn things around." Gorshow stresses the importance of correct timing when deciding to ask out your friend. "Timing is the first thing," said Gorshow. "Is this guy already interested in someone? If he is, then he probably will not be looking in your direction. Make sure he is available and not interested in anyone else."

The Taken Friend

What happens when you fall for someone who is separated from their partner, yet not divorced for whatever reason? Gorshow suggests strengthening your friendship before pursuing more. "Be prepared that they might not yet be ready for a new relationship. They may not yet be emotionally separated from their partner. For this reason, I suggest that you approach spending time with them as two friends enjoying each other's company versus two people going out on a date. This may seem to you as a matter of semantics, but the change of wording may be enough of a difference for her to feel emotionally ready to spend time with you. Who couldn't use a friend after being separated from a partner? Besides, it is always better when two people start a new relationship as friends first."

Is Your Friend Interested?

"Your friends may be of assistance with finding out this information," said Gorshow. "Once you know with certainty that he is free and clear, it's time to move on to the second item on your list, getting him to see you differently. When two people know each other for a long time, they sometimes miss the romantic signals each is giving out. To test the waters, you need to step up the flirting."

Sending Flirting Signals

Flirting is a fun way to let a guy know you are interested without risking rejection. "To get his attention, you might want to try dressing in a way that is different than usual," said Gorshow. "You can try a new clothing color, a different style, or do up your hair differently. You don't want to overdo it; even something as simple as changing the way you usually do your makeup is enough to draw attention to you. He may not notice it right away, but it is likely he will notice that there is something different about you. This change will make flirting a lot easier because it will already have drawn his attention to you."

Don't Rush the Relationship

"Usually, two people show interest in each other through the medium of flirting," said Gorshow. "Flirting leads to wanting to spend time together through the medium of dating. If there is chemistry and mutual interest, then dating can lead to a relationship. You are so focused on getting a boyfriend that you're missing the steps it takes to get there. In other words, don't tell someone that you like them before you're sure the feeling is mutual."

Finding Opportunity

"Once you know he is available and you've done something different to draw his attention, you'll now want to create opportunities to spend some time together," said Gorshow. "Whether you invite an even number of guys and girls over to your place, or to go someplace and do something, you'll want to give yourself the opportunity to talk and flirt with him alone. Here is where you'll notice his level of interest. If he is not showing interest or you're not sure, ask a friend to test the waters for you. Once you're sure he is looking at you differently rather than just a friend, you can move on to suggesting that the two of you hang out together sometime. By suggesting rather than asking, you are taking a safer risk and putting the burden on him to follow through."

From Friends to Romance

"One of the downsides to developing a romantic relationship with a friend is that many times what you gain in romance you lose in friendship," advised Gorshow. "If two of you start going out and the relationship ends, so may the friendship. So think long and hard about what you want because you may just get it."

Staying Friends

How do you stay friends if you try a relationship and it doesn't work? Open communication is the key as is a mutual desire to remain friends if the romance doesn't work out.

Take Baby Steps First

There is no reason to rush things when it comes to wanting to date a friend. Take your time and wait until the moment is right; a desperation to be with someone can lead to bad decisions. Think things through before acting for the best results.

Advice on How to Ask a Friend Out