Trying To Choose Between Two Men? Ask These 15 Questions

You never expected to be torn between two guys. This is the stuff of romance novels and reality TV. 

And with one or both of them pursuing an exclusive relationship with you, it’s time for a difficult choice. You’ve enjoyed your dates with both of them. The competition is fierce. 

When it comes to choosing between two men whose company you enjoy, you need to go beyond the kinds of questions you ask when you’re just getting to know each other. 

Fortunately, you’ll find 15 such questions below. 

Can you have feelings for two guys?

Having romantic feelings for two people at once is more common than you might think. And thinking, “I like two guys,” doesn’t make you a bad person. It’s not easy to be faced with the question, “Which man do you choose?”

Here are your options if one of them is asking for an exclusive relationship:

  • Say yes and immediately put the other guy on notice. 
  • Thank him but ask for more time to consider what he’s asking. 
  • Say no, taking the risk he’ll push you away and pursue another. 

Obviously, if you’re not sure yet which man to choose, response #2 is the safest option. But getting closer to a yes or no answer is the goal here. 

How to Choose Between Two Men: 15 Questions to Ask 

The following questions will help you decide what to do when choosing between two guys. Answer them carefully and honestly for both of the guys you like. 

1. What does he want from the relationship?

You can also ask, “Where does he see the relationship headed?” Is he thinking, “Let’s move in right away so we can really get to know each other”? Or is he more inclined to continue living separately for a while until you get to know each other better? 

How much time does he want to spend with you during the week, and what does he want to do with you? Is he already thinking of marriage and kids, or would he like to date for a few years before even considering “the M-word”?

2. Do you want what he wants?

When he describes the kind of relationship he wants with you, do you want that, too? Does his idea of moving forward match yours? 

woman and two men sitting on stairs wearing face masks choosing between two men questions

Would you be ready to move in with this guy if he asked? Or would you feel pressured to go faster than you want? Would you rather live separately but spend time together in each other’s homes — maybe your place one night and his place the next? And how often?

How do you picture your time together?  And are your goals compatible?

3. What do you enjoy doing together? 

Aside from the predictable romantic shenanigans, what do you two enjoy doing together? 

When it comes to going out, where do you both like to go? Do you have enough in common that you find it easy to settle on what to do? Do you ever feel as though one of you gets to choose more often than the other does?

Do you enjoy competing with each other? If so, is he a good sport? Or does he get sullen or depressed if the results fall short of his expectations?

4. Can he be open and vulnerable with you? 

Have you had any heart-to-heart talks where he opened up to you? Does he feel comfortable enough to be vulnerable with you?

Maybe you’re the only one with whom he feels comfortable opening up. Or maybe he’s an open person who’s not afraid to be vulnerable with anyone he cares about. 

Or maybe he’s just not there yet. You’ve had some deep conversations, but you can still feel a wall between you. What would it take to remove it?

5. Do you share the same morals or values?

Would you vote for the same person in the next election? Or do any of your moral beliefs or values clash? 

Do you find it stressful or impossible to talk to him about certain moral or political topics? 

You don’t have to agree on everything, but do you agree on the dealbreakers? Or are you hoping to persuade him to your way of thinking? 

6. What do you like about this guy? 

Make a list of all the qualities you like about each guy. Circle the qualities most important to you. Make a separate list of qualities you want to see but haven’t seen yet. 

friends hiking choosing between two men questions

When have you noticed their admirable qualities? Is it possible they were on their best behavior to impress you? Or were they displaying those qualities when they thought no one was looking?

7. What do you see in this guy that bothers you? 

What do you see in each guy that raises red flags? Has he said or done anything at all that made you think, “Uh-oh”? 

Think about all the times you’ve spent together and be honest about whether he made you feel uncomfortable at any point. For example, has his behavior suggested he likes to be in control? Or have you noticed him checking out other girls?

Maybe what bugs you is harmless stuff like forgetting to put the toilet seat down. Write it down, anyway.


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8. Do your friends like him for you? 

Ask them what they liked about each guy and what they didn’t. If you really want to put them on the spot, ask them which one they’d pick for you. 

Granted, this is your decision to make. But you want to know if your friends have a bad feeling about one of these guys. Real friends won’t want you to be stuck with someone who gives them a bad vibe.

Ask them for their honest appraisals and give their words thoughtful consideration. 

9. Do you get along with his friends?

If you’ve met both guys’ friends, ask yourself which set of friends you’d rather spend more time with. If you haven’t met the friends of the guy who wants a serious relationship, is there a reason he hasn’t introduced you to them?

woman thinking while man in the back looking at her choosing between two men questions

It’s not a deal-breaker if he doesn’t have a big circle of friends. Maybe he only has one good friend. Or maybe he gets along with most people but only opens up with you.  

In any case, you should know what kind of people he likes to associate with. And ideally, you’ll enjoy their company, too. 

10. Would you be together if sex was not an option?

Whatever the reason, if sex wasn’t something you’d be doing together, which of these guys would you rather spend time with? And what would you do together? 

This is an important question to answer because if sex is the only reason you’re keeping one (or both) of these guys around, you’re unlikely to be in a serious relationship for very long. 

Who would be the most fun to hang out with? Or which one of them makes it easier for you to be yourself but also inspires you to keep learning and growing?

11. Would you call him if you had a bad day?

You’ve just gotten some terrible news, and you’re in tears. Which of these guys would you be more likely to call? Which do you feel more comfortable crying with? Or have you ever been that vulnerable with either one of them? 

Maybe you’ve just had a crummy day, and you want to spend time with a guy who will just let you chill and enjoy something without grilling you with questions. 

Which of these guys is emotionally available yet respectful of your privacy?

choosing between two men infographics

12. How do you feel when you’re with him? 

Think about the best time you spent with each guy and remember how you felt when you were with him. Then think about the worst time you spent with each guy and do the same. 

Compare the lists for each guy, and draw jagged lines under any feelings that stand out as red flags for you. How you feel when you’re around him matters. You want to feel as though the guy you spend time with sees you as his favorite conversation partner. 

Pay attention to the red flags. In a serious relationship, those tend to get worse. 

13. What do you talk about with him?

What do you usually talk about when you’re together. Is there a lot of small talk at first, or do you jump right into a meaty conversation about something? Do you ever run out of things to talk about? 

Which of you does most of the talking? Do either of you launch into a multi-tangent monologue that leaves the other looking bored or slightly panicked? 

Do you find you talk about the same things whenever you’re with one of these guys? Or do you slip right into an easy conversation about whatever interests you both?

14. What topics do you avoid with him? 

Are there any topics of conversation that are off-limits with either of these guys? Think about your conversations and which ones, if any, veered into uncomfortable territory. 

woman in the middle of two men posing for the camera choosing between two men questions

Did you disagree about something important to you? How did he handle it? Did you both decide to simply avoid the subject? And how does that make you feel when you want to talk about that subject with him — but you don’t dare? 

It’s exhausting, isn’t it? You don’t want to walk on eggshells around the guy you spend so much time with. And if there’s one subject off-limits, there will be others. 

15. How is he handling life?

What challenges does each guy face, and how is he handling it? Does he make the best of the good things in his life — his gifts, his resources, his time? If he has debt, is he responsible, or is he constantly using credit cards to buy things he doesn’t need?

Does he work, and is he dependable? Do you rely on his good sense and compassion? Or have you expressed concern about his behavior? And if so, how did he react?

Does he respond to stress with addictive or reckless behavior? Or does he strike you as a mature man who knows who he is and what he’s willing to fight for? 

Are you able to choose between two men now?

Now that you know the questions to ask, take the time to do each one justice, for both men’s sake and for yours. Use whatever helps you answer these questions in full: 

  • Write the questions and answers in your journal.
  • Ask a friend to go through the questions with you. 
  • Talk to a counselor about the situation. 

You want the result of your decision to be the best possible result for all three of you. It’s an emotional situation with high stakes, so be patient with yourself. 

Whatever you decide, let your intuition and your good sense guide you.

When choosing between two men whose company you enjoy, you need to go beyond the kinds of questions you ask when you’re just getting to know each other.

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