5 Questions To Ask A Date When You Want To Take It Further

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I've always believed that when you first start dating someone new, the best policy is to keep things light and low-pressure. Just figure out if you like the person, enjoy their company, and see if you have good chemistry. Most of the time, even though the person is great, they just aren't the right fit for me because they don't hit all those criteria. However, when they actually do and it's time to start taking things to the next level, I get a little nervous. Thankfully, I've learned to have serious questions to ask a date on standby that will help me decide whether or not to take things further. These are questions that can aid you in getting a little deeper and gaining a better understanding of who the person is at their core, but also what kind of future they envision for their lives. That way, you can tell if that's even a picture you want to be a part of.

Knowing how to ask those questions and get good, illuminating answers can be challenging, though. So, I reached out to the experts for their advice on which questions you should ask to make sure you are really on the same page before you take your relationship to the next level. Here is what they had to say.

How many committed relationships have you been in?

While talking about all your exes with a new potential partner is probably not the best plan, it doesn't mean knowing more general things about their dating history can't be really helpful and important when you're deciding to take things to the next level. This is why Connell Barrett, Dating Transformation founder and executive dating coach, tells Elite Daily a good question to ask is about the number of committed relationships they have had in the past. “You want to get a sense if this person is able to commit,” he explains. “If the answer is zero, then that's a bit of a red flag or at least a yellow flag because you don't know if he or she has the experience to be a good partner. We learn from our mistakes and relationships so you want to find out if this person has already gotten some experience in being a committed relationship partner.”

Do you see yourself having a family one day?

When you picture the future, do you see a possibility of having a family someday? Or maybe you’re sure that's just not in the cards for you. How does your potential partner feel? If you don't know the answer to that question, Barrett says you should ask it before getting too serious in the relationship. “Having children together potential is one of those big life things that we have to have in alignment with another person or else there is going to be long term life problems. Better to find that sooner rather than six months in when you’re in love and you find out you want totally different things in terms of family,” he says.

What was the very best day of your life and why?

Not all of the important questions have to be heavy and high-pressure. In fact, this one can be a lot of fun to ask and answer — while still being extremely illuminating. “It sparks a great conversation,” says Barrett, which makes it ideal for asking early on in dating. However, it also gives you some real insight into the person's priorities. “When someone tells you what the best day of your life was they are basically given you the blueprint for who they are as a person,” says Barrett. "[For example], if they say the best day of their life was the day they got a big promotion and the corner office, that person is really career-focused. [Or] if the best day of their life was the surprise party that their family threw for them when they turned 21… that person is telling you their main blueprint is about connection, love, and family. There is no wrong answer to this question. What you want to do is listen to their answers and find out if the underscoring emotional experience of why the best their life was the best day of their lives — and if that's something you vibe and connect with,” he explains.

What do you see for yourself in the next few years?

Once you have been dating for a while and you feel that the relationship really is going somewhere, it's a good idea to get a picture of what the future may look like together, as Diana Dorell, intuitive dating coach and author of The Dating Mirror: Trust Again, Love Again, tells Elite Daily. This is why she suggests asking questions that will give you some insight into what your potential partner's plans are in the next few years. “Ask this in a light way and it will give you insight into the type of lifestyle and goals the person has. If you see yourself on the same page with what they are sharing that is a good sign. If not, it is a revealing question that will help you exit the relationship before it gets too serious,” she says.

A few questions you should ask yourself before taking things further.

Getting some insight into where you partner is at and what they want from life is essential if you are going to go the distance, but Dorell says it's also important that you own needs and happiness don't get lost in the mix. That is why she suggests checking in with yourself before going further in the relationship. “One thing to ask yourself — not them — that's important to whether this goes to the next level is: ‘Do I enjoy who I am when I'm with them? Do I genuinely like them as a person aside from all the attraction? Would I be friends with them?’,” she says. If the answer to those questions isn’t yes, then it's time to consider pumping the brakes on the relationship, at least for now.

Asking serious questions can sometimes feel a bit awkward or intimidating, but relationships are built on good communication. So, not only are you finding out whether or not a person is a good fit lifestyle-wise, but these kinds of conversations are also a great way to see how well you will communicate in general. Whew, sometimes adulting is hard, but then when you do find that person that is your perfect fit, suddenly it’s all worth it. Also, dodging the bullet of a bad fit is pretty great too. Just saying.

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