20 Important Questions You Should Ask Your Crush (3 of 4)

“When was your last relationship?”

Piggybacking off your headway into dating in general as a topic, you can probe a bit further about your crush’s last relationship, or why it didn’t work out for them, or something along these lines. Shelly Kessinger from Friendswood Marriage Counseling says that this question can be a goldmine, as it allows you to understand your crush better and see how they behave in a relationship. You not only get to know the duration of time that has elapsed since that last relationship; you also get to know more about them.

“Why did it fail/end?”

If the previous question was a success and you got your crush to talk about their previous relationship, you should press a bit and ask why their relationship failed. You get to know a lot about them, including whether or not they are self-aware to analyze how their relationships have fared so far. If you notice them referring to their ex as someone who was “crazy”, you should beware as they very well could say the same about you. By asking this question, also try to assess how they describe themselves in their previous relationship. Are they bitter, angry, annoyed, or relieved about their past relationship? This can also help you judge their emotional availability, and give you a sense of what they consider as deal-breakers.

“Are you over your ex?”

This can be a tricky question, but it is an important one if you want to know if they are open to a relationship right now. While their answer can be yes, it is a chance to reflect, points out Kessinger. The question allows them to communicate what they feel inside. You should focus on their answer and see if there is any bitterness, annoyance, or resentment, says Kessinger. The key is focusing not just on what they say, but also on how they say it, points out Kessinger.

“What is your love language?”

If you aren’t aware of what your love language is, find out what it is! Learning more about your crush and their love language can allow you to generate a deeper bond with them without having to expose yourself emotionally too soon, says Chloe Miller, CEO of And, Swipe Right. This is how so many people get that ‘they understand me so well’ relationships going on for them, she points out. Being able to communicate in your crush’s language can help them feel heard, seen, and emotionally validated. It is quite a flattering experience and would strengthen your bond with them.

“What activity makes you relax and wind down?”

We all like to wind down and relax at the end of the day, and quite similar to probing whether they are an extrovert or an introvert, you should ask your crush if or how or what they do to relax at the end of a day. The key here is to see if you share common grounds here. If you both find something similar, such as yoga to relax and wind down, you should bond over that activity, says Miller. It doesn’t always have to be fun, and as long as it helps you both spend time together, it can be a great way to bond and develop deeper affection.