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20 “What If” Questions To Ask Your Boyfriend

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Playing twenty questions is a lot of fun, but asking the same old questions over and over again is definitely not. You have to keep the questions fresh in order to keep the appeal of the game. However, it can be really hard to think of great questions to ask on your own! Once in awhile you might find yourself needing a little help. Especially if you want to ask him questions that appear to be a bit more serious. Sometimes you will find that you want to get him thinking long and hard about your relationship. It’s not always easy to gauge just how committed to you he is. Lucky for you, we’ve created this list of 20 what if questions for your boyfriend. This gives you the perfect opportunity to do just that!

What if I gained a lot of weight? How would you react?

His Answer Should Be: I’m not going to go anywhere if you gain any weight. I’m with you because I love YOU for you, not for your looks.

An Okay Answer Would Be: I wouldn’t mind, but we should try to be healthy people. I don’t want us to feel bad about ourselves.

 A Bad Answer Would Be: Don’t gain weight babe, I hate when girls get fat. It’s just so ugly. I don’t think that I could deal with it.

What if I was very sick? How would you care for me?

His Answer Should Be: I would make sure you had everything you needed. I want to be you as comfortable as possible. If you need to go to the doctor or need me to make you soup, I’m there!



An Okay Answer Would Be: I would give you a lift to the doctor, but probably no kissing until you are better.

A Bad Answer Would Be: I wouldn’t want you to come near me. I would not risk getting sick just to spend time with you.

What if I told you I was pregnant? How would you react?

His Answer Should Be: I would be happy as long as we are together and can commit to raising this child together. I would love to have a family with you someday!

An Okay Answer Would Be: It’s not ideal, but I would take responsibility for my actions..

A Bad Answer Would Be: We would have to figure out a way to get rid of it, because I can’t see myself having kids with you. I don’t love you that much.

What if I got sent away for a long time?

His Answer Should Be: I’d wait for you! I would visit you as often as I could and be there for you when you return. I’ll miss you a lot, though.



An Okay Answer Would Be: I would wait for you, but I can’t promise that we wouldn’t drift apart eventually. I hope not, though.

A Bad Answer Would Be: I would probably breakup with you. I don’t think I’m serious enough about you to wait for you.

What if my best friend was hitting on you?

His Answer Should Be: I would reject her advances and then I would come to tell you immediately. After that I would only go around her if you said it was okay to do so.

An Okay Answer Would Be: I’d laugh it off.

A Bad Answer Would Be: Well, I can’t help myself if a pretty girl comes on to me. What do you expect me to do?

What if my parents stated that they hate your guts?

His Answer Should Be: I would be very disappointed. I would also try to work really hard at making them not hate me. They aren’t my parents, but I love you so I’ll tough it out.

An Okay Answer Would Be: That would suck, but it’s whatever. I still love you.

A Bad Answer Would Be: I don’t really care. They don’t matter to me at all.

What if my ex messaged me and asked me to take him back?

His Answer Should Be: Well, he’d be wasting his time because I would never let anyone steal you from me. I’m yours and you are mine. I love you!

An Okay Answer Would Be: Please don’t talk to him again. That guy really bugs me.

A Bad Answer Would Be: I’d probably let him have you.

What if I found out I was terminally ill?

His Answer Should Be: I would stand by your side, holding your hand. I would take care of you until you’re very last breath. I would pray everyday for a miracle, because seeing you die would be the most devastating thing to ever happen to me.

An Okay Answer Would Be: That would suck.

A Bad Answer Would Be: I don’t think I could deal with a sicko for a girlfriend. I’d probably wish you the best and be on my way.

What if there was an apocalypse?

His Answer Should Be: I would find you right away and we could start figuring out what to do from there. No matter what happens we will face it together!

An Okay Answer Would Be: I wouldn’t know what to do, to be honest.

A Bad Answer Would Be: I would get the heck out of here, but I don’t think I could bring you with. You might just slow me down.

What if I needed somewhere to live by tomorrow?

His Answer Should Be: Of course I would let you come live with me. I would never let you sleep on the streets!

An Okay Answer Would Be: I don’t think we are ready to live together just yet, but you are welcome to stay with me until you find another place to live.

A Bad Answer Would Be: I don’t think that is a good idea. Can’t you find somewhere else to stay?

What if I lost my job tomorrow?

His Answer Should Be: I’d be there to listen to you vent! After you have talked it out, we can start looking for a new job that you can apply to!

An Okay Answer Would Be: I’m not really sure, but I’ll be here for you no matter what.

A Bad Answer Would Be: I don’t think I can be with someone who is unemployed. I don’t date bums.

What if you had a chance to change one thing about me? What would you change?

His Answer Should Be: I would never change a single thing about you. I think that you are perfect the way you are!

An Okay Answer Would Be: I might change the fact that you talk a lot during movies, but that’s about it.

A Bad Answer Would Be: I would change (something about your physical appearance) because it really bothers me.

What if I could fast forward 5 years, where would I see you? What would you be doing?

His Answer Should Be: I’d be with you, obviously. Hopefully building a life together!

An Okay Answer Would Be: I hope to excel in my career by then or pay off my debt.

A Bad Answer Would Be: Living a single life, with no one to nag at me all day.

What if you could only pick one goal/dream to follow? Which would you choose?

His Answer Should Be: To start building a great life with you.

An Okay Answer Would Be: To get that big promotion at work!

A Bad Answer Would Be: Who needs goals? I’m just here to have a good time.

What if you won the lottery?

His Answer Should Be: I would buy us a house together, a new car and pay off our debts.

An Okay Answer Would Be: Finally catch up on all of my bills and debt so that I can live a little easier.

A Bad Answer Would Be: Vacations all day everyday. Pretty women and booze for life!

What if our love started to fade away?

His Answer Should Be: I don’t think that would ever happen. I love you too much.

An Okay Answer Would Be: I would try to not let that happen.

A Bad Answer Would Be: Well they say once the flames out that it’s out for good. Guess we gave it our best shot.

What if we lived far away from each other?

His Answer Should Be: I would write, call and visit every chance that I get!

An Okay Answer Would Be: I would try to make it work.

A Bad Answer Would Be: I don’t think I can do a long distance relationship. I think if that happened, it’d be best to see other people.

What if you could meet me a second time? What would you change?

His Answer Should Be: I wouldn’t change anything, because I am happy with how things turned out. I might try to impress you a little harder.

An Okay Answer Would Be: Probably nothing.

A Bad Answer Would Be: I don’t really care. This question is dumb.

What if you got one wish and you could wish for anything?  What would it be?

His Answer Should Be: To give us the perfect life! Or anything that would make you happy!

An Okay Answer Would Be: I would wish for a lot of money, because being broke sucks.

A Bad Answer Would Be: A hotter girlfriend, duh.

What if you had to describe me in 3 words? (The words can be interchanged with similar words.)

His Answer Should Be: Beautiful, amazing, smart.

An Okay Answer Would Be: Cute, stubborn, loyal.

A Bad Answer Would Be: Naggy, mean, prudish.

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