Where do you see yourself in 5 years?

Recently, my friend shared a video with me in which a lady was relating her first date experience with a guy. The guy had asked her on their first date what her plans were for the next five years and she was taken aback by this “pettiness” as she called it. According to her, this was totally inappropriate and it made her wonder if she was on a date or at a job interview.

She didn’t let this slide. She retorted with her own question — she asked the guy what his retirement plans were. Of course, she wasn’t really interested in the answer, she merely asked it as a sarcastic way to let the guy know that some questions, such as his question, are just not appropriate. Apparently, the guy took offense at this and that pretty much ended their date.

After seeing the lady’s video about this, the guy published his own video in response. He reasserted his stance on the matter and said that he saw nothing wrong with the question he’d asked. He said he asked this question because he wouldn’t date or marry a person who doesn’t have a life plan or a sense of purpose.

I wanted to get other opinions on this matter so I posted it on my WhatsApp status and found that many of my friends saw no problem with the question. They agreed with the guy that they too would only date or marry a person who is purpose-driven and has a plan for their life. They emphasized that knowing this at the beginning is essential as it would help them decide whether to proceed or end the relationship at an early stage, thereby saving themselves the time and resources that might have to be expended on subsequent dates.

A few other friends expressed a different opinion. Like the girl, they felt it was not courteous to ask such a question on a first date.

This disparity in opinions over this question reminded me once again that we humans are very different from one another in the way we think. A rude comment to one person can be received as a compliment by another person. Because of this, I don’t suppose I am in the position to say who was right and who wrong. Nobody is. I think people are just different. I will merely state how I would interpret such a question if I were to be on the receiving end of it on a first date.


To aid with my explanation, I am going to paint a hypothetical scenario. I am on a date with a lady and she asks me, “Where do you see yourself in 5 years?” A minute of silence ensues during which I lift my glass of iced fruit juice from the table between us with all the poise I can muster and draw a long sip. This gives me enough time to process her question.

If she takes my silence to mean that I am thinking of a perfect answer to give her, she is mistaken. I am not thinking about the answer; I am thinking about the question.

I recognize that question. It is a very old question and it is also very cliché. It is most popularly known for being used at job interviews to judge whether a candidate is a good fit for a position or not. Because of this, asking this question might make the person asking it seem slightly condescending or even rude.

Asking me this question immediately tells me that she very overtly wants to know if I am a good fit for her or not. She is evaluating me and makes no effort to conceal it. You’ve got to presume yourself to have a kind of high ground over a person before you can ask them that kind of question. That is why I do not find it polite at all.

Come to think of it, this is our first date. Do you expect me to spill my plans for the future with somebody I am hanging out with for the first time?

We need to first build the foundations of trust. We need to be sure that we are comfortable around each other and that we find each other’s company pleasant at least. We will need some time to verify again that the chemistry is there and we did not just whip it up in our imagination. This down-to-business approach on the first date suggests to me that she doesn’t view any of that as important.

Don’t get me wrong, I am not against having a kind of plan for your future. But this is just not the time and asking that question is just not the best way to find out. 

Asking the question might actually prove to be ineffective. Even if I articulate an impressive vision of my life in 5 years, how can she tell if I’m not just making a wish rather than saying something I’m determined to work towards achieving? Having a plan for the future is important but what is more important is the qualities you embody in the present. Qualities like consistent effort, strategy, determination, persistence, perseverance, sound moral principles, and more. 

If someone had asked me 5 years ago what my plans were for the next 5 years, whatever answer I gave them would have been a lie. Sure, in my own vague way I had plans but if I had stuck with them, I would have settled for far less than was possible. Life in this fast-changing world can be full of fascinating twists and surprises and new opportunities. A plan for an imagined future might be important but what is even more important is the qualities you embody today and the values you live by here and now. Your 5-year plan might change, but who you are now and the values you live by will not. 

Asking me that question actually raises suspicions in me: Is she interested in the person she is seeing before her right now or in the version of me that shall have achieved their dreams 5 years hence? If tomorrow I am the victim of some misfortune, and the plans I had shared with her fail to materialize, will she love me any less because of it? Will she tell me with disappointment that I have “changed” or that I am not the man she thought I was? Maybe my suspicions are false. Maybe they are not. But it would be best if she doesn’t give me any reason to be suspicious at all. This is just another reason why it is probably a bad idea to ask that question.

I know some people would argue that asking this question will help them know if they are a suitable match or not. But I have already made an argument against this: it is not effective; there is very little you can tell about a potential partner by their answer to this question, and given the nature of the question and the potentially negative effects it might elicit on your date, it is not worth asking.

The years don’t go by in leaps of 5. Who I am in all the months, weeks, and days that make up 5 years is just as important if not more important than where I end up in 5 years. It would be more effective to check for values that a person can exercise here and now. You can know in just a few moments of being with a person if they are kind, smart, hardworking, committed, persevering, and so on, and based on this, you can safely guess if they are purpose-driven and if they have a bright future ahead of them.

Purpose is a journey. It is not a specific instance in the future. Sure, it can culminate in something; it can lead towards something, but the journey is just as important. That is why it is possible to live a purposeful life without necessarily having a clear picture of your life in 5 years.

Now, there is another way to look at this. She could have asked this question for any number of reasons. Maybe she asked this in an innocent attempt to keep the conversation going or to dispel an awkward silence. Maybe she was just nervous and some people, particularly me🙈, say things that don’t make sense even to them when they are nervous.

Maybe asking the question doesn’t say anything about her that I should be concerned about. Maybe she was not asking it to evaluate me or anything like what I’ve said so far. On its own, the question might mean anything or nothing.

So it might be too early to form any strong opinions about her on the basis of one question she asked. It is good to give people the benefit of doubt. It is only when you identify a sustained pattern of such quirkiness that you can make something serious of it and probably take appropriate action. e.g. talk about it with your date.

Like I said at the start, people are different. I have discussed this with friends and they seem to consider this question to be some sort of an effective pickup line for them. So if you feel like taking a risk, go right ahead and ask it. But you should know that you are treading on thin ice. The question is a dealbreaker for some people.

To come back to my case, I think in the end I will probably answer her question just to be polite, but making sure I reveal only as much as I feel comfortable to reveal.


I would very much like to hear your thoughts on this. What do you think about this question? How would you feel being asked this question on your first date? Let me know in the comments below.

Thanks for reading 😊