325 Questions to Ask When Checking Up on Someone

Checking up on someone? Asking the right questions can help you understand what they’re going through and show that you really care. Whether it’s a loved one going through a hard time or significant life event, a friend starting a new job, or an elderly relative, the right questions can open the door to meaningful conversations. 

So, let’s dive in and explore some smart, thoughtful questions to ask when checking up on someone.

Questions To Ask Someone With Mental Health Issues

1. How have you been feeling lately?
2. Is there anything you’d like to talk about?
3. Are there any specific things causing you stress or anxiety right now?
4. How have you been sleeping recently?
5. What activities have you been able to enjoy recently?
6. Have there been any changes in your appetite or weight?
7. Are there moments when you feel better or worse?
8. Do you have someone to talk to when you’re feeling low?
9. How is your energy level these days?
10. How are you taking care of yourself?
11. Are there things you’ve found that help you feel better?
12. Do you feel like your feelings are manageable most of the time?
13. Has it been hard to focus or concentrate recently?
14. Are you comfortable with your current treatment or therapy?
15. Do you feel your medication (if any) is working?
16. What’s something good that happened to you this week?
17. Have you been able to get out and exercise or be in nature?
18. Are there tasks or activities that feel too hard right now?
19. What’s one thing I can do to support you right now?
20. How are your relationships with friends and family?
21. Do you feel like your mood changes a lot?
22. What’s something you’re looking forward to?
23. Have there been times when you’ve felt really hopeless?
24. Have you been spending time on hobbies or activities you enjoy?
25. How do you feel when you wake up in the morning?
26. Are there certain situations or people that make you feel worse?
27. Are you feeling more irritable or agitated lately?
28. What’s one positive thing about your day today?
29. Is there anything you’re worried about in the future?
30. Are there things you used to enjoy but don’t anymore?
31. Are you feeling physically unwell or in pain?
32. How are you coping with your daily responsibilities?
33. Do you feel like you’re in control of your emotions?
34. Are there times when you feel really anxious for no clear reason?
35. Are there certain thoughts that you can’t get out of your head?
36. Do you feel isolated or alone, even when you’re around people?
37. Are there any memories or experiences that have been bothering you?
38. Is there anything that’s happened recently that’s been hard for you to handle?
39. How often do you feel overwhelmed?
40. Do you feel your worries are rational or irrational?
41. How do you usually relax or unwind?
42. Is there anything that has made you feel happy or peaceful lately?
43. Do you find it hard to motivate yourself to do things you need or want to do?
44. How are you managing any negative or harmful thoughts?
45. Are there any big changes in your life recently that have affected you?
46. Is there anything that you’re currently afraid of or anxious about?
47. Are there times when you feel disconnected from yourself or your surroundings?
48. How has your overall mood been in the past few weeks?
49. Do you feel like your feelings are impacting your life a lot?
50. How often do you feel fatigued without a physical reason?
51. Do you feel like you need more support in dealing with your feelings?
52. Have you had any thoughts of self-harm or suicide? (Note: Only ask this if you feel prepared to handle the answer. Always reach out to a professional if someone you know is in danger.)

Questions To Ask Someone During A Job Transition

1. How do you feel about leaving your old job?
2. What is the new role you’re moving into?
3. What excites you most about this new job?
4. How did your first day/week go?
5. How are you adjusting to the culture of your new workplace?
6. What are your primary responsibilities in the new job?
7. How is the commute to your new job?
8. Have you made any new friends or connections at your new job?
9. Is there anything that you find challenging about the new job?
10. What are the biggest differences between your old job and the new one?
11. How does the new job align with your long-term career goals?
12. How have you been managing the work-life balance in the new role?
13. Do you need to learn any new skills or tools for this job?
14. What support have you received during this transition period?
15. How does the workload compare to your previous job?
16. What’s your favorite part of your new role so far?
17. Is there anything you miss about your old job?
18. How is your relationship with your new manager and colleagues?
19. Have there been any unexpected surprises in your new role?
20. Is there anything I can do to support you during this transition?
21. Do you feel like the new position is a good fit for you?
22. Have you had a chance to apply your past experiences and skills in your new job?
23. What kind of projects are you working on right now?
24. How do you feel about the new company’s mission and values?
25. Have you received any feedback so far in your new role?
26. Are there any opportunities for growth and advancement at your new job?
27. How have you been handling stress during this transition?
28. What’s the team dynamic like in your new workplace?
29. Are there any particular goals you aim to achieve in your new position?
30. Have there been any memorable moments since you started your new job?
31. Do you have a mentor or someone guiding you in your new role?
32. What’s one thing you’ve learned since starting this job?
33. Are there any perks or benefits in your new job that you’re particularly enjoying?
34. How has the job change impacted your daily routine?
35. How is the new job affecting your overall life satisfaction?
36. How are you taking care of yourself during this transition?
37. What are your expectations for the first few months in this role?
38. How do you plan to contribute to your new company or team?
39. Have you had any doubts or concerns since starting the new job?
40. How has your family reacted to your job transition?

Questions To Ask Someone During A Financial Crisis

1. How are you feeling about your current financial situation?
2. Would you like to talk about what’s been going on?
3. Are you taking any steps to manage your finances?
4. Do you have a budget or a plan you’re working with?
5. Are you getting any financial advice or counseling?
6. Is there anything I can do to help right now?
7. Have you reached out to any organizations for financial assistance?
8. Have you considered speaking with a financial advisor?
9. Are you struggling to cover basic needs like food and shelter?
10. How are you managing stress during this challenging time?
11. Are there any unnecessary expenses you could cut down?
12. Do you have any sources of income at the moment?
13. Are there any jobs or opportunities you’re looking into?
14. How is your family dealing with the situation?
15. Are there any financial goals you’re aiming for right now?
16. Are you able to meet your debt obligations?
17. Have you thought about setting up an emergency fund?
18. Do you plan to rebuild your finances once the crisis is over?
19. Do you want to share any lessons you’ve learned from this experience?
20. Are you communicating with your creditors about your situation?
21. Have you thought about creating a savings plan for the future?
22. Are you exploring different options for increasing your income?
23. How are you keeping up with your mental health during this time?
24. Have you looked into government or non-profit assistance programs?
25. Are you being careful to avoid scams and quick-fix schemes?
26. Is there a way you can reduce or consolidate your debts?
27. Have you thought about investing in financial literacy or budgeting courses?
28. Is your financial crisis affecting your relationships with family or friends?
29. Are you making any changes to your lifestyle to help with your situation?
30. Are there any resources or books you find helpful in managing your finances?
31. Are you familiar with your legal rights as a debtor?
32. Have you considered seeking legal advice regarding your situation?
33. Are there any habits you’re changing to better manage your money?
34. Are there certain expenses you find particularly hard to cut down on?
35. How are you explaining this situation to your kids, if you have any?
36. Have you reached out to friends or family who have been in a similar case for guidance?
37. What are you doing to maintain a positive outlook despite the financial challenges?

Questions To Ask Someone After A Loss

1. How are you holding up since the loss?
2. Do you feel comfortable talking about your loved one?
3. Is there a memory of your loved one you’d like to share?
4. Are you taking care of yourself and getting enough rest?
5. How are other family members coping with the loss?
6. Is there any specific way I can help or support you right now?
7. Would it help to talk about how things happened?
8. How are you handling everyday tasks and responsibilities?
9. Is there anything you’re finding particularly challenging right now?
10. What’s something about your loved one that makes you smile?
11. Are there times when you feel particularly sad or overwhelmed?
12. Have you considered seeking support from a grief counselor or support group?
13. How are you dealing with moments of loneliness?
14. Is there something that helps you when you’re missing your loved one?
15. Have you been able to connect with friends or social activities?
16. What are some ways you’re keeping your loved one’s memory alive?
17. Have you been able to spend time outside or exercise?
18. Are there people you can lean on when you’re feeling down?
19. Do you have any concerns or worries about the future?
20. Is there anything you need right now that you’re not getting?
21. Have you found any comforting rituals or routines?
22. How do you feel about being alone right now?
23. Are there any tasks or responsibilities you’d like help with?
24. Have you been able to get out and do things you enjoy?
25. Do you find it helpful to write or express your feelings creatively?
26. Are there any moments of relief or peace in your day?
27. Do you feel like you’re able to grieve in your own way?
28. How are you handling nights and bedtime? Are you able to sleep okay?
29. Is there something that triggers a lot of sadness for you?
30. Have you been having any dreams about your loved one?
31. Are there any upcoming dates or events that you’re worried about?
32. Do you feel like you have enough support from the people around you?
33. Are there any books, movies, or songs that have been comforting?
34. Are there any decisions or arrangements you need help with?
35. Are there days when you feel more hopeful?
36. Have you noticed any changes in your physical health?
37. Is it helpful for you to keep a journal or diary of your feelings?
38. How are you coping with milestones or anniversaries without your loved one?
39. Have you spoken to a professional, like a counselor or therapist, about your grief?
40. Do you find it helpful to connect with others who’ve had a similar experience?

Questions To Ask Someone Who Has Recently Moved

1. How do you like your new home?
2. What do you enjoy most about your new neighborhood?
3. Have you had a chance to meet your neighbors yet?
4. What was the move like? 
5. Did everything go smoothly?
6. Are you finding everything you need in your new area?
7. Have you started exploring the local area?
8. What’s the biggest difference between your old place and the new one?
9. Is there anything you miss about your previous home or location?
10. How have you decorated or personalized your new place?
11. How are you getting to work or school from your new place?
12. Have you found any cool local spots like parks, restaurants, or shops?
13. How is the rest of your family adjusting to the new place?
14. Did you have any unexpected challenges during the move?
15. How do you feel about the change? Are you feeling settled in?
16. Have you made any new friends in your new area?
17. Is there anything about your new location that surprised you?
18. Are there any upcoming events you’re looking forward to in your new community?
19. Have you had any challenges getting used to the new place or community?
20. How does the cost of living compare to your previous place?
21. Is there anything I can do to help you settle in?
22. Have you managed to establish a routine yet in your new place?
23. Have you found a new favorite place to relax or have fun?
24. What’s the funniest or most interesting thing that has happened since you moved?
25. How did your first few nights go in your new home?
26. Are there any new local foods or dishes you’ve tried and enjoyed?
27. How are you handling any homesickness or feelings of missing your old place?
28. Have you found any clubs, teams, or groups to join?
29. Is there anything about the culture or customs of your new area that you’re still learning?
30. Have you had any issues or problems in your new home that needed fixing?
31. How are the seasons or weather different from your previous home?
32. Is there anything in your new neighborhood that reminds you of your old one?
33. How are your pets (if any) adjusting to the new place?
34. Are you keeping up with hobbies and interests in your new location?
35. Have you found a new doctor, dentist, or other important services yet?
36. Has the move changed your daily commute?
37. How is the pace of life different in your new location?
38. Have you had a chance to host any guests in your new home yet?

Questions To Ask When Checking Up On A New Parent

1. How are you and the baby doing?
2. Are you getting any sleep? 
3. How are you handling the night shifts?
4. What’s been the most surprising thing about being a new parent?
5. How is your baby feeding?
6. Have you been able to take some time for yourself?
7. How is the baby’s routine shaping up?
8. What’s been the most rewarding moment so far?
9. How are you balancing the needs of the baby with your own needs?
10. How has your relationship with your partner changed since the baby came?
11. Is there something about parenthood that you weren’t prepared for?
12. What kind of support do you need right now?
13. How are you feeling emotionally?
14. Has your baby reached any new milestones recently?
15. What’s been your go-to technique for soothing your baby?
16. Have you found any helpful resources for new parents?
17. How is your baby interacting with other family members?
18. Have you started thinking about childcare options for when you return to work (if applicable)?
19. Are there any new parent worries or anxieties you want to talk about?
20. How has your daily routine changed since the baby arrived?
21. Is there anything I can do to help or support you during this time?
22. Are you enjoying your time with the baby?
23. How has the transition been with the new family dynamics?
24. Is the baby in good health? Any concerns or issues?
25. How have you been keeping up with household chores and duties?
26. Has the baby developed any likes or dislikes yet?
27. Are you taking plenty of photos and videos to capture these moments?
28. How are you managing outings and appointments with the baby?
29. Have there been any funny or unexpected moments so far?
30. How do you cope when the baby is fussy or crying?
31. Are you still managing to eat well and stay hydrated?
32. Have you had your postnatal check-up yet, and how did it go?
33. Has the baby started recognizing you or responding to your voice?
34. How are your older kids (if any) adjusting to their new sibling?
35. Do you get time to connect with your partner amidst the new responsibilities?
36. How is your baby’s sleep pattern? Are they sleeping through the night yet?
37. Are you using any apps or gadgets that help with new parenthood?
38. Have you received any parenting advice that you found particularly useful?
39. Do you have a support network you can rely on when things get tough?
40. Are there any parenting books or resources that you’ve found helpful?
41. What’s the best thing about being a new parent?
42. How have you been handling visitors and introductions?
43. Are you finding any baby gear particularly helpful?
44. How has the adjustment been for your pets, if you have any?
45. What’s something about your baby’s personality that you’re beginning to notice?

Questions To Ask When Checking Up On Someone In School

1. How was school today?
2. What was the most fun thing you did today?
3. Did you learn anything interesting today?
4. How are your classes going?
5. Are your teachers nice?
6. Who are your best friends at school?
7. Is there anything you’re having trouble with at school?
8. What’s your favorite subject, and why?
9. Are you getting along with everyone okay?
10. Have you had any cool projects or assignments lately?
11. Did anything funny happen at school today?
12. What’s the best book you’ve read for school recently?
13. Do you have a lot of homework tonight?
14. Are you looking forward to any school events?
15. What did you have for lunch at school today?
16. Do you like your school uniform or dress code?
17. Is there a teacher you like or who helps you a lot?
18. Are there any subjects or classes you wish you could change?
19. How do you feel about your grades right now?
20. Is there anything you wish was different about school?
21. Do you feel safe and comfortable at school?
22. What are some new things you’ve learned recently?
23. Have you joined any clubs or teams?
24. How’s the school food? Do you like it?
25. What is the hardest part of your day at school?
26. What kind of homework do you enjoy the most?
27. Is there something you’re excited about learning?
28. Who inspires you at school and why?
29. Are there any upcoming tests or projects you’re worried about?
30. How do you usually spend your breaks at school?
31. Have you read any interesting books for school lately?
32. Are there any new rules at school that you don’t like?
33. How’s the journey to and from school? Is it easy or tough?
34. What’s the one thing you would change about your school if you could?
35. Is there a subject you’d like more help with?
36. How do you feel about the amount of homework you get?
37. Have you met any new friends recently?
38. Is there anything about school that’s been making you feel stressed?

Questions To Ask When Checking Up An Elderly

1. Are you keeping up with your doctor’s appointments?
2. How have you been sleeping?
3. Are you eating well and staying hydrated?
4. Are you able to get around okay, or are you having any mobility issues?
5. How are you keeping yourself busy these days?
6. Are you keeping in touch with friends and family?
7. Is there anything you’re worried or anxious about?
8. Are you taking your medications properly?
9. Are there any new health issues or concerns you’re dealing with?
10. Have you been able to get outside for some fresh air?
11. Are there any activities or hobbies you’ve been enjoying recently?
12. Do you need help with any chores or tasks?
13. Have you seen or read anything interesting lately?
14. How has your mood been overall?
15. Are there any upcoming events you’re looking forward to?
16. Is there anything new or different in your daily routine?
17. How’s your comfort level at home? Are you staying warm/cool enough?
18. Do you feel safe in your surroundings?
19. Is there anything you need that you don’t currently have?
20. Are you managing to stay active?
21. Have you been able to maintain your independence?
22. Have you had any falls or accidents recently?
23. How are your energy levels these days?
24. Have you been experiencing any pain or discomfort?
25. Have you been finding things to laugh about or enjoy each day?
26. Do you ever feel lonely or isolated?
27. Have you been having any issues with your vision or hearing?
28. Is there anyone you wish you could talk to or see more often?
29. Have there been any changes in your weight?
30. Are there any community activities or groups you’ve been part of?
31. Are you able to easily prepare meals for yourself?
32. Do you need help managing your finances or bills?
33. Have there been any changes in your memory?
34. Have you noticed any changes in your strength or balance?
35. Are there any upcoming appointments or events you need help preparing for?

Frequently Asked Questions

Conclusion

With these questions in your toolkit, you’re all set to show the people that you care about their well-being. Remember, the most important thing is to listen—really listen—to their answers. It’s not just about asking the right questions; it’s about being there for them, showing empathy, and offering support.

So, go on and reach out to someone who could use a chat—it could mean the world to them.