Questions to Ask Your Mom's Boyfriend
Questions for getting to know the man your mother is seeing: easy ground for a first meeting, and the more direct ones worth asking once you have met him a few times.
The questions
Open any question for the note
How did you two meet?
Why ask it
The safest opening, and you often get two versions if your mother is in the room. It lets him talk without feeling assessed.
What do you do with your time these days?
Why ask it
Works whether he is working, retired or between jobs, which a question about his career does not.
How do you and my mom usually spend a weekend?
Why ask it
Tells you what the relationship actually consists of, which is more informative than how either of them describes it.
Where did you grow up, and are you still in touch with anyone from there?
Why ask it
The second half is the useful part. Friendships that have lasted decades say something a biography does not.
Do you have children, and how often do you see them?
Why ask it
Reasonable to ask and worth knowing. How he talks about his children, and about their mother, tells you a great deal in one answer.
What are you like to live with?
Why ask it
A disarming question most people answer honestly and with some humor. A flattering or vague answer is worth noting.
What did you first notice about her?
Why ask it
You learn whether he sees your mother as a person or as a role. Specific answers are a good sign; generic compliments less so.
What do you two disagree about?
Why ask it
Every couple has something. A man who says they never disagree is either very new to this or not being straight with you.
What do you want your role in the family to be?
Why ask it
Better asked than assumed. Answers range from wanting to be a fixture at every occasion to being clear he is not trying to be anyone's parent.
How would you like me to introduce you?
Why ask it
A practical question that saves awkwardness at gatherings, and it signals you are willing to make room for him.
What should I know about you that she probably hasn't mentioned?
Why ask it
Hands him the microphone. What he chooses to volunteer, and what he leaves out, is itself information.
What do you do when the two of you argue?
Why ask it
The most useful question here if you have any concerns. Listen for whether he describes repair or withdrawal, and who tends to apologize.
How do you think holidays should work, with both families?
Why ask it
Concrete logistics that will otherwise be decided badly in December, and it shows whether he has considered your side at all.
What's been hardest about coming into a family that was already there?
Why ask it
Invites honesty rather than reassurance, and most people find it easier to answer than a question about their intentions.
Where do you see this going?
Why ask it
Direct, and fair to ask by the second or third meeting. Notice whether his answer matches what your mother believes.
Have the two of you talked about living together?
Why ask it
Questions about a shared home tend to surface everything else: money, property, and who else would be affected.
How do you two handle money?
Why ask it
Only worth asking if you have a reason, and better asked plainly than hinted at. Note whether he answers or hands the question to your mother.
What would you want from me if she were ill?
Why ask it
Serious, and it shows whether he sees himself as responsible or as a guest. If your mother is older, this is not hypothetical.
What do you think she needs that she doesn't ask for?
Why ask it
Tests whether he pays attention. Good answers are small and specific; a man who cannot answer at all may not be looking.
Is there anything you want to ask me?
Why ask it
Turning it around ends the meeting as a conversation rather than a vetting, and what he asks shows what he has been nervous about.
Meeting your mother's partner
Practical guidance for the conversation itself
The first meeting
Pick a setting with an exit
Coffee or a walk beats a long dinner. An hour is enough for a first impression and short enough that nobody has to keep performing.
Ask him things, not about him
Questioning your mother about him while he sits there puts everyone on edge. Address him directly and let her stay out of it.
Save the serious questions for later
Money, intentions and illness are fair topics, but not while you are still shaking hands. They land very differently on a second meeting.
What to pay attention to
- How he talks about former partners and about his own children.
- Whether he answers for your mother or lets her speak.
- Whether any long friendships exist, and who those people are.
- How he responds to a question he would rather not answer.
- Whether your mother behaves differently when he is in the room.
Common mistakes
Comparing him to your father
Out loud or silently, it makes a fair assessment impossible. He is not applying for that job.
Raising money too early
If you have real concerns about finances or property, that is a conversation with your mother first, not an ambush over lunch.
Deciding on one meeting
People are stiff and defensive when introduced to adult children. Two or three ordinary occasions tell you more than one careful one.
Going quiet instead of saying it
If something worries you, say it to your mother plainly and once. Silence followed by cold politeness is worse for everyone, including her.