One Thing You Should Never Feel While Dating

A sort of unsettling term has been brought up to me relatively frequently lately during discussions about dating concepts. Particularly who should pay on a date (hint: It’s the guy). In one of my more recent articles about why paying for the date is not about the moneyI came across yet another comment using this same word. Unfortunately, it mostly seems to be women who are feeling this way.


What is the term?


Women, for some reason, are feeling more and more obligated when a man takes them on a date. The only man I can speak for is myself, but I know if I offer and choose to take a woman on a date, I am doing so because I want to. She is under absolutely no obligation to:

Pay the next time we go out.

Sleep with me.

Go out with me a second time.

Like me at all.

And the list goes on. A date is simply a chance to get to know another person and gauge any potential of a second date, and then a third, fourth, and so on. If any of the above things happen because of how well two people click together, then great! And if not, then great! You have simply found another person who has showed you qualities that you don’t want in your future teammate.

I don’t know what it is causing the feeling of obligation lately. The feeling that as a woman who is taken out by a man, you now owe him something. I don’t know if it is the increasing independence of women that is making them feel as though they cannot be taken care of without feeling guilty about it. I don’t know if it is the way men are approaching dates and if they are the purveyors of such nonsense. But what I do know is, it’s not the way things should be.


As a man who offers to take a woman on a date, I want to go pick her up. I want to open the door for her, and I want to take care of the bill. It is my way of showing her that I am interested and am willing to put in effort for her and to make sure she enjoys herself. For me, seeing this makes me have a good time as well.

For that reason, I require nothing in return – I am already getting a “return,” if that’s what you want to call it, by her having fun. This is also why I am increasingly picky about the types of women I take on dates. Should a real date not be reserved for someone with real potential? Perhaps men are just throwing things against the wall to see what sticks. They are not really picking and choosing the woman they want to spend time with, they are just scouring Facebook and Tinder until someone says yes.

I’ll give you an example – recently I went on a date with a woman whom I picked up, of course. We went to a rather nice restaurant in Boston, where of course I picked up the tab. I will never let my date see the total or pick up the bill, I simply slide my card into the bill folder, and that is that.

While we were waiting for the valet service to bring the car around, she walked over to one of the workers and paid for the valet, without me even knowing about it. Then we went somewhere else for a drink and when I stepped away from the bar for a moment, I came back to find the bill paid.

She made it very clear to me that she wanted to contribute and to reciprocate. This, to me, showed me the same desire for the evening that I had – to do something special for someone else and make sure everyone has a good time. We then went to a (free) show in the Boston Commons, enjoyed the rest of our evening, and I dropped her off. Everyone was happy and felt special. Even, pleasantly surprised. Reciprocation, not obligation. 


But the bottom line here is that there should be absolutely no feeling of obligation from either person when it comes to dating. There is certainly no way a solid foundation for a relationship can be built from a “what’s in it for me?” attitude.

If you feel that someone is just doing things for you in order to get something in return, it should go without saying that their intentions are clearly not genuine and if you’re looking for something serious, it’s probably best to look elsewhere.

Dating is not a science experiment nor is it an “eye for an eye” mentality where if I do for you, you must do for me. A healthy relationship cannot be built by a giver and a taker – for the giver will become eventually exhausted and unappreciated. It also cannot be built by a taker and a taker, for neither will ever get what they want.

Healthy relationships must be built on a foundation of give and give. Two people willing to give to each other to make their partner happy, finding their own happiness in return. When their happiness is your happiness, you know you have found love.

There are a lot of things someone should make you feel when you are together, but obligated is never one of them.


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6 thoughts on “One Thing You Should Never Feel While Dating

  1. “Healthy relationships must be built on a foundation of give and give. Two people willing to give to each other to make their partner happy, finding their own happiness in return. When their happiness is your happiness, you know you have found love.”

    Very well said!

  2. Really like your “give and give” concept. I was never a fan of the ‘give and take’ ideology – never quite clicked with me. I always felt that one should never have to take; that if one person in the relationship isn’t willing to give, it’s a sign it won’t work out. ‘Give and take’ is built around the idea that if I give something, now I’m entitled to something. I prefer your “give and give” – it just feels better.

  3. The values of obligation and desire are and always have been interlinked when it comes to being old school gentleman. It’s not an expectation to be projected onto our partners or women, but the fact you felt the need to make a distinction between being obligated and wanting to do something is probably just your new school thought. Study history and you’ll now where it’s from – and yes people should always give for the love of giving in loving relationships, but the reality is dating is a numbers game and what we hold true in loving relationships is not necessarily something we need to bring into the dating world.

  4. If I know half way through dinner or ?? I am never going to see this man again, not as a friend, not as anything and am doing that “what the hell was I thinking?” I offer to pay for myself. Why? got nothing to do with anything except that it makes me feel better about myself, not offering seems rude. If he insists on paying, I thank him graciously and don’t argue. But if I like the guy enough for a second connection then I let him pay -sometimes these
    “things” are just not logical nor need (to me) they be.

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