Questions to Ask Your Boyfriend to Test His Loyalty
Questions about loyalty, boundaries and honesty for someone who wants a real conversation with her boyfriend rather than a confrontation, with notes on what different kinds of answers usually indicate.
The questions
Open any question for the note
How do you define loyalty in a relationship?
Why ask it
A definition built only out of things he would never do is thinner than one that also includes things he actively does. If the answer is a shrug and 'just not being a jerk,' he has probably never had to think about it.
What boundaries do you think matter for a couple like us?
Why ask it
People who have thought about this name situations: work trips, late-night messages, drinking with one particular friend. People who have not will say boundaries are for couples who do not trust each other.
What does being faithful mean to you beyond the physical side?
Why ask it
Watch whether emotional closeness with other people registers for him at all. Someone whose only line is sex often has no language for the confiding and secrecy that usually comes first.
How do you handle it when you find someone else attractive?
Why ask it
Flat denial is the least believable answer available, and it usually means he thinks the honest answer would upset you. What you want is a description of what he does next: says nothing, keeps distance, tells you.
When has someone flirted with you while we've been together, and what did you do?
Why ask it
Asking for a past instance rather than a hypothetical changes the question completely. Anyone can describe the ideal response; far fewer can recall having actually done it.
How would you want me to handle it if someone hit on me?
Why ask it
This is where double standards surface. If the rules he sets for you are tighter than the ones he just described for himself, that gap is your answer, and it is worth naming out loud.
Do you think people can stay close friends with an ex?
Why ask it
Answers cluster into no contact, occasional contact, or an ongoing friendship he has not mentioned to you before. The third one is not automatically a problem, but it is the one to ask calmly about.
Who do you talk to when you're upset with me?
Why ask it
A sibling or an old friend is unremarkable. A confidant you have never met, or someone he finds attractive, is the shape most emotional affairs start in.
Do you talk to your friends about our sex life?
Why ask it
Plenty of people tell one close friend and see no harm in it. What matters is whether he can say where his line is without being cornered into it, and whether his line is anywhere near yours.
Has a friend of yours ever said something disrespectful about me, and what did you do?
Why ask it
Listen for tense. Men who would rather keep the peace with their friends answer this in the conditional, describing what they would say, and never in the past tense.
Have you ever cheated on anyone before?
Why ask it
The yes or no matters less than the account after it. Someone who has thought it through can describe the run-up and his own choices; someone who has not will describe it as something that happened to him.
Have you ever lied to me about something that mattered?
Why ask it
Expect a pause. A quick cheerful no to a question this broad is less reassuring than a small awkward admission, because everyone has one.
What would make you consider ending things with me?
Why ask it
Deal-breakers show you what he is watching for and what he believes he is owed. 'Nothing, ever' is flattery rather than commitment, and it tends to mean he has not imagined the relationship being hard.
What's your biggest worry about us?
Why ask it
Worries are more informative than promises because people rarely invent them on the spot. Whatever he names is the place he already senses the relationship is thin.
What's something you've done for us that you don't think I noticed?
Why ask it
This lets him point at evidence instead of intentions. If nothing concrete comes to mind, he may be relying on how strongly he feels about you rather than on anything he has actually done.
Would you tell me if you started having feelings for someone else?
Why ask it
Almost everyone says yes, so the useful follow-up is how he would say it and when. People who mean it have already pictured the conversation; people who do not will stay abstract.
If I asked to look through your phone tonight, how would that land with you?
Why ask it
Discomfort proves nothing on its own; some people find the request insulting as a matter of principle. The difference worth noticing is between 'that would hurt my feelings' and a change of subject.
If we hit a stretch where we were both unhappy, what would you actually do?
Why ask it
Look for a process: raise it, talk, counseling, wait it out. An answer about how much he loves you skips the question, which is about behavior under strain rather than feeling.
Is there anything going on that I don't know about?
Why ask it
Ask it once, plainly, then stop talking. The silence afterwards does more work than any follow-up, and rushing to soften the question is what lets a vague answer pass.
What would you need from me to keep feeling secure in this?
Why ask it
Closes the conversation with something each of you can act on, and tests whether he can state a need without turning it into a complaint about you.
How to have this conversation
Practical guidance for the conversation itself
Before you start
Decide what you are doing
There is a difference between wanting to know how he thinks about loyalty and suspecting something specific. If it is the second, say so directly. A set of questions used as a trap tends to produce a fight about the questions rather than an answer.
Pick a time with no exit
A long drive, a walk, a Sunday morning. Not the ten minutes before he leaves for work, and not after either of you has been drinking. If he can end the conversation by standing up, he probably will.
Ask three, not twenty
Twenty questions in one sitting is an interview. Choose the three you most want answered, ask them slowly, and let the rest come up over weeks.
Answer them yourself first
Say your own definition of loyalty out loud before you ask for his. It changes the conversation from assessment to comparison, and it is much harder to be evasive with someone who has just been specific.
Reading the answers
Past tense beats conditional
'I would never' costs nothing. 'Last spring someone at work kept messaging me and I told her I was seeing you' costs something. Push gently for examples whenever he answers in the hypothetical.
Watch for the answer to a different question
A common move is to answer the question you did not ask: you ask what he did, he tells you how much he loves you. That is not a lie, but it is not an answer either. Repeat the original question once, calmly.
Note what he manages you away from
Irritation at a specific question is worth more attention than the content of any single answer. So is over-explanation, especially detail you did not ask for about times and places.
One bad answer is data, not a verdict
People say clumsy things about hypotheticals they have never faced. Look for a pattern across several questions, especially a gap between what he expects of you and what he expects of himself.
What tends to go wrong
Testing on a loop
If you ask the same question three months later hoping for a different answer, the question is no longer about him. Repeated testing erodes the relationship whether or not he has done anything.
Treating phone access as proof
A clean phone shown on demand proves that the phone is clean right now. It is weak evidence either way, and building the relationship around it usually makes both people worse.
Explaining away a clear answer
If he tells you he sees nothing wrong with something you find unacceptable, you have your answer. The temptation is to decide he did not mean it. Write down what he said instead.
Ignoring what you already know
If you came to these questions because of something you saw, no answer here replaces that. Ask about the specific thing. General questions about loyalty are a way of avoiding the conversation you actually need.