Is Asking Out A Friend A Bad Idea?

Updated April 10, 2024by Regain Editorial Team

Asking someone out is an exhilarating, intoxicating, and terrifying feeling. Even a confident person is entitled to feel nervous and begin sweating, shaking, or trembling before or during the actual asking portion of asking someone out. If you receive a "yes," though, success! And if you receive a "no," you still have the satisfaction of knowing that you took a risk and went for something (someone) that you wanted.

Asking out a friend can be tricky

Not all love interests are created equally, however. If you ask out the barista at your favorite coffee shop, you might run the risk of having to find a new place to get your morning coffee. If you take a chance on dating a coworker, you might be staring at the face of extreme awkwardness at work, and you might feel as though you have to transfer to another department, or even find a new place to work. But perhaps even more worrisome than a barista or a coworker is the idea of asking out a friend. Is asking your friend out always a bad idea? How do you ask a friend out?? How different is dating your best friend from dating other types of people in your life? What about flirting with a friend versus dating a friend?

Before you ask your friend out, flirt a little. Flirting can be a casual way of gauging someone's interest in you, and can help both of you feel more at ease around one another. If you flirt with your friend and they seem to return your interest in kind, you can begin to think about taking the next step in pursuing romance. If, however, your flirting is met with a blank stare, discomfort, or displeasure, you will have a clear window into where you stand in your friend's eyes, and you need not risk the hurt or embarrassment of going through with asking them out.

Flirting with a friend is much safer than actually dating your friend. Flirting is usually harmless, fun, and commitment-free, and offers a way to be close and candid with someone, without the added baggage, fear, and uncertainty of actually pursuing a romantic entanglement. If you are interested in your friend but do not want to risk your relationship, flirting is the safer way to go.

Dating your best friend

Dating your best friend can be a wonderful thing. Many people end up believing that their partners are their best friends, so dating your closest friend might simply take some of the time out of the whole process, and mean that you are actually ahead of the dating and marriage curve. Your closest friend will likely know your past, your dating history, your likes, and your quirks, and may have already come into contact with your shortcomings. This means that there are fewer surprises in your relationship, and the two of you already know that you have some amount of compatibility with regard to your personalities and preferences.

The flip side of that, though, is that dating your best friend doesn't afford a lot of surprises, which can be one of the most exciting parts of a new relationship. If you savor the feeling of not knowing what comes next in a relationship, you might feel you are missing out when dating your best friend. You might also struggle with knowing the ins and outs of your closest friend's past. If you've been friends for a while, you have likely seen them through at least one breakup, and may have heard the more sordid details of their past romantic dalliances. Although this might not matter to you, some people might find it difficult to date someone they have been through the trenches with.

Deciding whether you should ask your friend out

Deciding to ask your friend out is a big decision, and it requires a decent amount of forethought before just jumping in. A friend should never be asked out on a spur-of-the-moment impulse, or on a whim, as this is a relationship you might lose if your date or romance goes sour.

Before asking out a friend, first think the options through. What will you do if your friend turns you down? How will you proceed if your friend offers you an emphatic "yes!" but your date fizzles out entirely? Are you ready for a long-term relationship, or are you hoping to engage in a casual fling with your friend? Answering these questions can help you determine whether or not asking your friend on a date is actually a good idea.

Asking out a friend can be tricky

In addition to seeing your question through to its possible conclusions, you should ask yourself why you want to date your friend, instead of seeking out someone else you might like. Is your friend the only person you can see yourself being with? Do you have a chance of finding happiness (or at the very least, fun) with someone else? If so, why is your friend a better candidate for your dating life? This isn't to definitively say no to asking out a friend, but can help you gain some clarity in figuring out why you want to pursue a relationship with your friend, and whether or not your motives are sincere, healthy, or wise.

Speaking with an unbiased observer can help you understand your motivations and ideas behind asking out your friend. You might initially feel like it is a great idea, only to discover that asking your friend out is a way to stack the odds in your favor, instead of actually seeking out a relationship you want to be in. Mutual friends and family are likely to have their own biases, but a therapist can offer some thoughtful questions and exercises to determine the motivation behind your actions. 

How to ask a friend out

Fortunately, one of the better things about asking a friend out, versus someone you aren't terribly familiar with, is that your friend knows you, and the two of you already have some basis of communication. Rather than having to muster up the courage to find your crush, come up with a good line, and complete the official question, you can simply talk to your friend about the idea, and ask their opinion. A simple "How would you feel if I asked you on a date?" could pave the way for an official ask-out, while keeping your friend and yourself in a place of responsibility and accountability. This way, your friend has the option to carefully offer a no and a reason, versus having to just turn you down, or put in their two cents about why it'd be a great idea—or somewhere in between, not saying "no," but not feeling quite certain about saying "yes," either.

Above all, be honest. Your friend does not deserve to be smooth-talked or lied to, nor does your relationship have a hope of recovering if you go into this type of relationship feeling cocky and careless. Keeping honesty at the root of your conversation will allow both of you to come to the table on even footing, with trust and emotional safety.

Is asking out a friend a bad idea?

Asking out a friend can yield one of the most joyful, compatible relationships you've ever experienced, or it can lead to tremendous pain and heartbreak. As with any other romantic relationship, the risks are high, and the rewards are similarly immense. On its own, asking out a friend is not necessarily a bad idea; with enough good humor, humility, and grace, the two of you can recover from a gentle letdown after asking your friend out, or from finding out that you simply don't work as a romantic couple.

In some cases, though, asking out a friend means asking for trouble; if the two of you both struggle with insecurity, have trouble setting boundaries, or experience difficulty saying "no," asking your friend out can be recipe for pain and discomfort for the both of you. This is one of the many reasons it is important to carefully consider all possible endings to your query. You and your friend are potentially putting yourselves in an awkward position, if your relationship doesn't work out, or your ask-out is turned down, so make sure you both have a good sense of humor, and thick skin about the situation, to avoid inadvertently hurting each other.

Ultimately, asking your friend on a date is neither good nor bad it is what you make it. If you feel strongly for your friend and want to see if the two of you can enjoy a romantic relationship, go for it. The worst that can happen is you get a "no," and the two of you feel awkward for a while until you can work back to just being friendly with one another. If your friend accepts your offer of a date, and you enjoy yourselves, you've added a wonderful new dimension to your relationship. If your friend says yes, the two of you date, and you discover that you just aren't right for one another, you can both handle the situation with kindness, compassion, and maturity, and your friendship can come out the other side—perhaps a little bit shaky—but not altogether broken or irreparable.

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