Here's the sitch: You had a crush on someone and asked them out. They said, "Sure! I just have to look at my cal and get back to you." Then you didn't hear anything. Maybe they were busy, or perhaps you had to go out of town. Suddenly, months have flown by, and you're still swooning at their Instagram stories! Sometimes, knowing how many times you should ask someone out before giving up can be seriously confusing. And this is true for a ton of different scenarios (not speaking from personal experience or anything, ahem!). Is it chill to ask them out again or should you just cut your losses and move on from this crush?

You have to make sure that you're listening, as well as being respectful. "If you ask a person out and they flat out say, 'no I don't want to go out,' then it is essential to let time pass — maybe a month, maybe six months, but you need to accept and respect their wishes," says Dr. Joshua Klapow, Ph.D. Clinical Psychologist and Host of The Kurre and Klapow Show. "If you are clear and they are clear that they don't want to go out, do not push and persist. It is rare that asking someone out gets misinterpreted." If you fear that it may have been misinterpreted, you can try being clear and considerate by adding a caveat to your original message (or IRL convo) in which you asked them out.

It's OK to be clear and direct when asking someone out on a date, which will make it more likely for your intentions not to be misinterpreted. Dr. Klapow also recommends that when you ask someone out, you find a balance of being direct and succinct. You don't want to miss the opportunity to communicate your interest!

Dr. Klapow also recommends that you push for more transparent communication early on, so you don't find yourself in a situation where you feel like you need to ask them out again without knowing if they're interested. For instance, if you ask someone out and they don't respond or if they change the subject without answer, consider trying the lines "Maybe another time?" or the more direct "Would you ever consider going out with me?" The person that you're asking out will likely be honest about their comfort and interest level so be prepared to listen and respect their wishes. It's so awesome that you're putting yourself out there and asking someone you're interested in on a date! That is pretty remarkable and brave. Part of this process is owning your decision, even if they aren't interested.

As far as rejection goes, if you do get turned down, don't underestimate how much it can just absolutely suck. "Rejection always hurts, it always feels very personal, and it is very common to attribute all of the rejection to yourself," he says. "It's imperative to listen to the person's response and even ask for information if they're comfortable sharing. Sometimes it's not about you and more about the place they're at." He also stresses that there's a vast difference between a person not wanting to go out and a person disliking you. "Yes, there is the pain of not having things go the way you wanted, but remind yourself that their rejection, unless stated, represents on their part just a desire to not progress things with you."

When you're struggling with disappointment, learning from an experience is the best way forward. It's best not to repeatedly ask someone out if they've turned you down. But if things are vague or unclear, it's best that you're honest and forward with them. And, if you shoot your shot but it ultimately miss, you can always just chalk it up to some solid practice for when the right person comes along.