Things To Ask On A First Date: Dating History

January 9, 2022

Ahh first dates- they are both exciting and nerve racking! No matter the amount of first date I’ve gone on and it has been more than my younger self would have expected in the search for love- I still get all those first date nerves because I have zero idea of what to expect, especially if this is a first date off of a dating app. Sometimes those first date nerves have led me to be less focused on the actual process of getting to know someone new and see if there is a connection, finding myself much more preoccupied with calming my nerves and keeping up with convo.  So as time has gone on, I have found myself taking note of the topics that have been discussed on past dates and how those have better helped me get to know someone new so that I can be better prepared for a first date despite the first date nerves. There are so many topics to bring up and then there are topics that you may want to ask but feel may not be for first date material. We could go on and on about what these topics are that we have thought about asking – but one of the areas that we are addressing today as being an important topic to broach on your next first date is dating history! It is something that may feel pretty direct to ask someone you just met but we feel that there are smooth ways to bring this topic into your discussion and many reasons why we feel it can be critical in getting to know someone romantically.

Why We Ask About Dating History On A First Date:

This is something that the two of us used to think was maybe too upfront to ask about on a first date or awkward to come out and directly ask until we both came to the realization that multiple guys have asked us this question on first dates. This made us realize that again our dating nerves have gotten the best of us making us overthink things that are totally typical to address on a date and actually makes a lot of sense to ask one the first date.  Why? Because in finding a match- one of the biggest factors is just finding someone who is available and has a desire for a relationship. While dating apps may have been created for dating purposes or thought to be used for that reason- there are tons of people on the apps who want to have fun and date around. So if you are looking to date people who are looking for relationships then you will want to weave out the ones who are just on the apps to date around and have fun with nothing serious.

In addition to weaving out those in the dating pool that are looking for the same thing you are- it is also helpful to understand this individuals relationship history to see if they are someone who is very much a relationship person, someone who has led more of a bachelor lifestyle, and someone who may be just getting over a breakup. Of course dating history doesn’t give you all you need to know but it can be helpful in getting to know that date and how they may date. We have had dates who have discussed interest in relationships but later on exhibited other behavior and then came to realize that they were someone who had been leading a bachelor lifestyle for most all of their adulthood and was likely not a match for ourselves. The opposite has happened too, where we have met someone who seems very much a relationship type of person which led them to seek out a relationship right after a breakup, a breakup that we later found out they were not at all over. Again you can’t base your decision off of one thing but we appreciate bringing up this topic to get more context and more helpful information. You never know, you could ask someone thinking they are very much looking to date for the purpose of a relationship to find out that they don’t believe in marriage or settling down any time soon and while there is nothing wrong with that if it doesn’t align with you then that isn’t the match for you!

How To Ask About Dating History:

So we know why this topic can be helpful to bring up on a first date but you may be wondering, much like we used to, how do you bring this topic up?! It may seem very personal to directly ask about their entire dating history which is why we have thought about the ways that we have been asked that have not felt too personal or uncomfortable to be asked by someone we just met that night. The ways in which we have best appreciated being asked this question and the ways that we have picked up on as being smooth ways to introduce this topic- have been led with something along the lines of-

“How have the dating apps been treating?”

“Have you been using the dating apps for a while or are you new to them?”

Some version of these two questions can further lead to more convo on whether they have been single for a while or if they are new to the dating scene. You never know where the convo will go from there but either way you can get some context that may be helpful in understanding what this individual may be looking for or how they date.

There are so many questions to ask and so many topics to discuss when getting to know someone but this is one that we have come to realize has been very helpful in the early stages of dating! For more on dating check out our dating and relationships section!