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50 Questions and Answers about Dating-A guide for men

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What to consider before starting?

– Dating may come easy to some, although making mistakes is even easier when emotions are involved. If finding a hook-up, or your partner for lifetime, is currently among your goals, then review the below list to make a reality check on how well you understand yourself and what dating is about. The list is long, because the process can also take a lot of time and effort, but you can look at it as a step-by-step guide: you don’t need to figure it all out at once. When you have your answer to a question, you can start working on the next with more confidence and a positive attitude.

2. Are there any issues or other priorities you need to sort out in your life first?

 – As already mentioned, dating will require a lot of your mental and physical energy – building up expectations, breaking ice with new people, happy moments and a bit of drama maybe, are all in store for you. If you have more pressing issues, however, like needing to focus on studies, work, a family member in need of help or another personal problem you are facing, you may not be able to give the needed attention to the person you want to date, or the issues may directly affect your attitude towards them and sabotage you to fail.

3. Are you looking for a serious commitment or a more casual affair?

– Knowing what you are looking for in advance is important. If you are aiming for a flirt or a short relationship, that is fine, just be careful not to misguide someone craving a long-term attachment, as that will lead to pain for them and most likely some headaches for you.

If you want a serious relationship, however, take some time to consider what that means for you and how far do you want to go on this path.

4. What qualities are you looking for in a person?

– Once you are certain you want to go on the dating front, set a list of qualities you want your partner(s) to have.It’s nice to be humble or romantic and say that you have no type or you will choose based on feelings, but you need to start the search somewhere. Think about personality, interests, looks, age group, maybe even profession and responsibilities that might be nice to have or will be too much for you.

5. Can you look for a date in your social circles or do you need to make new acquaintances?

social media, connections, networking

        – How is your social life going? Based on your previous answers, is there a person among your friends that matches the description and is also available? Do you have friends you can ask to introduce you to some of their colleagues or maybe some interest-based events you can visit? If no one you know seems to be a good match or you are just more introverted and like to keep to yourself, you can start exploring options to meet new people that will fit you better.

6. Where to find new potential acquaintances?

– If your friends are not able to help you or you just want to figure this out on your own, here are a few options. You can try to look up local activities related to your interest such as interest clubs or training classes, or you can also join online forums and groups on topics that you like, hobbies, music, sports, books, some science that you find interesting, games etc. Alternatively, I’m sure you know there are also dating apps and websites – they are many and some look for specific target groups, too – no need to limit yourself to just one. Keep in mind that the last option is best suited for one-time things and short term affairs, as it is difficult to find people interested in long-term commitment. For flirts, hitting bars, night clubs and other entertainment facilities might be most suitable.

7. Is there a line you are not willing to cross?

– Knowing your boundaries will also help you navigate the scene and the contacts you make in order to date. For example, if you hate superstitions, don’t try to get involved with someone who is into astrology or witchcraft, if you have a strong political view, avoid people who will be upset by it, if you are more free-spirited, don’t approach a conservative person who will try to impose their values on you etc. They might be hot, or have some other impressive qualities, but it won’t be worth the trouble.

8. What are your strengths and unique qualities?

 – You will need to present yourself in your best light in order to charm the person (or people) of interest. Try to make a list of the qualities that you like most about yourself or that have brought you advantages in your life so far. Later, when introducing yourself in person or when creating an online profile, find a way to display them or to at least mention them in a favourable way. Maybe it’s your smarts, or your looks, or your unique sense of humour, maybe you are a good listener or you have amazing skills in an area of your life. Don’t underestimate anything you excel at or that separates you from the rest. Cuteness and style are also traits that can make people look your way.

9. What are some insecurities you have that may be in way of your success?

– Very often people don’t realize that they are setting themselves up for failure just by making up reasons why it won’t work out. It can be something your family or friends told you numerous times that you are bad at or that it will keep you from success. If you don’t figure out what it is, it will hold you back as you will have less confidence and you will avoid situations that put your insecurity on the spotlight. Don’t miss opportunities because of fear of rejection. Take some risks.

10. What qualities can you work on to win over people you like?

– Aside from your core identity, which you just evaluated on the previous items, there are skills and qualities which anyone can obtain to function better socially and to be more approachable and likable. Maybe you don’t compliment often enough the people around you or you don’t take interest in what’s happening in their daily life. Or you’ve heard that you don’t smile often enough, you avoid eye contact, appear too distant. While looking for a date, try to hone your soft skills. If you feel like it, pick up a new healthy habit, learn about curious topics, try to improve some aspect of your looks (it can be fitness level, hairstyle or even just trying out a new type of clothing item or accessory). Small adjustments in the right direction can help boost your self-image and resulting charisma.

11. What are some red flags to avoid when looking for a date?

red flag, warning, danger
Photo by dimitrisvetsikas1969 on Pixabay

– It’s best to avoid people who promote some sort of hate speech as they will probably look for things to judge or bully you for as well. You can also look for signs that the person is too self-absorbed. It’s ok to talk about achievements and have a positive self-image, but it’s  another thing to constantly boast about oneself and not let any other person or object receive attention. If they mention their exes too often, that is also a red flag. Last but not least, keep your eyes open for any signs of tendencies to lie about major life events or back away if they mention suspicious or criminal activity.

12. How to approach a new person for the best outcome?

– Try to look for any similarities, or just open a chat about something you like about them at first glance; show genuine interest in the person; if it’s online and they said on their profile that they like funny guys, consider to open with your favourite joke or something funny you came up with on the spot. Keep in mind that not everyone will show interest, but that is no reason to be discouraged. Your luck will come eventually.

13. How to continue the first conversation?

–Pay attention to the style they are using and try to mimic it if possible – if they are formal, don’t go overly friendly, and vice versa. Have a set of topics you have tested before or just go with the flow if you see that the other person is receptive of your advance. It’s common to ask about biographical information like place of origin, occupation, hobbies etc. Try to expand the conversation and stay on topic for as long as it feels comfortable.

14. What are good conversation topics?

–Well, depends if you are a “small talk” type of person or a “deep thinker”. If you relate to the first, finding a topic probably comes easy to you, just be careful for any signs that the other person is bored and if that happens, switch to a different subject. If you don’t like small talk, however, you need to be careful not to go into someone’s personal space too fast – try discussing a trending matter in your community or something else you’ve found that people are hyped about lately – then hopefully you’ll be able to jump to various related topics.

15. What subjects should you avoid talking about?

– Try not to give your opinions unless you are being asked to, as some people will become upset and interpret it as patronising; Oversharing is often a turn-off when you’ve just met the person, unless they open up to you first; Do not comment on your previous relationships unless the other person shows interest about your past;  Avoid being too pushy too early.

16. When do you suggest a meet up?

– Inviting the person to spend alone time with you can be a big step to take and needs to be well calculated. If they’ve showed some obvious signs that they like you or that they enjoy talking to you, that’s great, even better if they first mention they want to meet. On the other hand, if they seem reserved or if you already had some disagreement or misunderstanding, you would do best to wait after you’ve had two or three more conversations to gain their trust before asking them out. If they avoid giving you a straight answer, things most likely won’t work out and you should look for other people.

17. What are safe ideas for a first date?

– If you want to get to know your date better and to enjoy a fun time together, you can go to some entertainment centre, a mall, a type of sport event or just a walk in a park or around the city. If you feel like just sitting and talking, invitation to coffee, lunch or dinner is always a classic. If your aim is to move things faster, you can still suggest a place where you won’t be interrupted by crowds or passer-byers, however, allow the option for either of you to leave with ease in case the mood changes. Don’t invite them over and don’t visit them in their living space; also don’t go to a cut off location that is difficult to reach.

18. How to prepare for the date?

– Assuming you’ve already set the location and you have a plan of what you want to do, you should choose your outfit accordingly. Make sure it is appropriate, not too formal, and fits the chosen activity and place. If you know that a certain colour looks good on you or highlights a part of your looks, bring it forward. Avoid experiments that cannot be undone if they went wrong – don’t try a new haircut the day before and don’t tire yourself out to the point that you won’t be able to enjoy the date. If you are too tense, find ways to relax and do something you enjoy to release the stress, and be ready to greet your date with a smile.

19. What are some do’s and don’ts when on a date?

– If your date does something you dislike or something in their look sets you off, don’t criticize them directly. At best, make a small remark and see if they will accept it or not; if you make a mistake in a conversation or activity you are participating in, make sure to admit it and apologize; and if a critical situation arises, make effort to help your date solve it – this will leave a lasting impression. Don’t enter their personal space if you see they are pushing you away and proceed with physical contact they are comfortable with only.

20. How to secure a second date?

– If the date went well, at the end you can thank them for the time and directly ask if they will be interested to repeat this. If there were any hiccups, you can consider following up with them later on call or chat to check how they’re doing and if they want to meet again. Try to finish the date on a positive note and to do something memorable to get in their head. If given the chance, offer assistance with something they are currently working on to stay in touch or mention some upcoming event that you would like to invite them to.

21. How to decide whether to keep seeing this person?

– Time to do some reflection on your experiences so far. Try to stick to your own judgement, but if you feel the need to, discuss with trusted people. If one or two friends are against this person, but you feel like they are unfair, it’s ok – you might have different needs and perspectives when compared to family and friends; however, if everyone around you for some reason advises you to stay away from this relationship, maybe they are seeing something dangerous that you are oblivious about or underestimate. The questions that follow will be focused to help you decide.

22. Do you have shared values?

– One of the main factors that drive decision making in people are their value and belief systems. If you happen to have opposing values, you will definitely disagree with the choices your date will be making in the future. If some principle is very important to you, and they disregard it, this will lead to frustration for you in future situations. Consider this carefully if you don’t want to face disappointments.

23. What are this person’s best qualities so far?

– Think about your conversations and time spent together. How did they impress you? What would you like to do again? What positive outcomes do you imagine? Do you feel happy thinking about this person? Do you feel the need to share or express your excitement? If needed, write the answers down and consider the significance of the qualities you appreciate in this person.

24. What are their annoying habits or harmful tendencies?

– Everyone has such. You do, too. What might be the things that irritate you, and are there any habits, believes, occupations and people around your newfound partner that might be a bad influence or that will lead to a harmful situation? Try to assess exactly how problematic this is for you and think about discussing it with them. Are they inclined to change? Will you be ok if they don’t?

25. How has your life changed after meeting this person?

– Compare your situation to before meeting this person. Did you gain anything, did you lose anything? Do you feel better about yourself or did your overall mental health take a hit? Did any relationships with friends and family suffer due to this person? Are you able to handle life struggles easier or do you face more difficulties as opposed to before? These changes in conditions will stay as long as this person is around, so take a careful look and decide if you like what you see.

26. When in their presence, are you a better version of yourself, or maybe a worse one?

– This one has a lot to do with how they are affecting your mental health. On the positive side, maybe you were always tense and anxious but with them you have more confidence in your actions and choices. On the flip side, though, you could be the friendliest and most cheerful person to be around, but when your partner shows up, you suddenly become irritable and start picking fights or just lose interest in anything.

27. Are you making any compromises with yourself when interacting with this person?

– Do you ever find yourself walking on eggshells and limiting yourself to please your new partner? Are there any hobbies you had to forgo, people you had to stop meeting, places you had to stop visiting? If you have arguments, are they ever resolved in your favour or does it always have to go their way? If the answer to any of these is yes, you have to work on standing your ground and if they don’t ever let you even try, they never valued you to begin with.  

28. Will you need to give up something to be with this person?

– At this point, you already know what this is – either your values, dreams, friends, hobbies or mental health. If you thought about all of this and you still feel that this is the person you are willing to change for, then continue to the next questions.

29. If you try to imagine a future with this person, what do you see?

plant, little plants, sow
Photo by congerdesign on Pixabay

–  Knowing everything you do now, close your eyes and try to imagine the next five, ten, twenty years with this person in your life. What goals can you achieve with them by your side? What events will make up your life? If you are convinced that’s the life you want to have despite the required sacrifices, and you are certain this person wants the same, then that is also fine. But if you have any doubts, check the next questions.

30. Are you settling for this person out of loneliness?

– If you answered the previous questions and found more negative sides to this person than positives, it is possible that you are with them simply to avoid being single. It is very common nowadays and people choose to lie to themselves and stay in toxic relationships out of fear of loneliness. If this person is making you more miserable than you were before meeting them, it’s time to put an end to this and move on. (More about this later in the article.)

31. How to make the relationship successful?

– You are now convinced this is the person of your dreams. You have left any doubts when considering the previous points and you want to be the best partner a person can wish for. The below questions will help you be considerate, respectful, understanding and fair in your relationship.

32. Do you understand this person’s schedule and day-to-day needs?

– It’s always nice to show care and concern about a person’s daily life. Even more so when you are supposed to have shared plans and have expectations of the other person. To avoid everyday misunderstandings and confrontations, it’s best to understand what responsibilities your partner has in their work and day-to-day tasks, what kind of people they spend their time with, how much free time they will have and how stressed they will be when they return back to you. This way, you can avoid uncalled for jealousy, arguments due to something that was expected of you to do etc. Ideally, your partner will also learn about your routines and needs and you’ll figure out how to complement each other’s schedules and needs. Discuss anything you are not sure about instead of assuming.

33. What are common activities you can both enjoy doing together?

– Based on your interests, put time aside for activities you can do together regularly. At least once a week, go out to dine or watch a movie or stay at home and play a game you both enjoy or listen to music while chatting, for example. You will know what works both for the both of you.

34. What are things they are neutral or disinterested about?

– It’s ok to have hobbies and interests that don’t match. However, no matter how passionate you are about yours, don’t try to push your partner to participate if they have showed strong lack of interest. Also make sure to mention those interests briefly and don’t go into unnecessary details. Do these hobbies on your own time and find friends to talk with instead.

35. Do you keep track of special events and make effort to show your affection?

– You are forming a bond with this person. You need to show them that you value them and that this relationship is important to you. You don’t want to make them feel forgotten or insignificant to you. To avoid that, be mindful of anniversaries, birthdays, other events that are important for them, and celebrate those occasions with pleasant surprises – can be a special plan for the day, a gift they’ve wanted for a while, cooking a special meal or any other display of affection you can think of.

36. Do you both share your worries about present or future events?

– Life is full of uncertain events, and people are no mind readers. Despite this, it’s easy to cave in and keep your worries to yourself; however, this will undoubtedly change your behaviour in ways that will make the other person question what is happening with you and start jumping to conclusions that might have nothing to do with reality. To avoid this, just share what’s concerning you, even if you don’t want to burden them or think they can’t help. In the same logic, when you see a change of attitude in your partner, inquire if they have any worries or a situation they can’t handle. Keep things clear of misunderstanding and always communicate openly.

37. Do you work on solving problems together?

– Following up on the previous point, discussing problems is of high importance to a successful relationship. Avoiding an issue doesn’t make it go away, and if only one of you is working to fix it, then the other most likely won’t agree with the solution. Do your best to hear out the other side and cooperate to find a good answer for the both of you.

38. Do you give each other space to breathe and be your own person?

– Not pushing your interests on your partner is one example of how to not suffocate them and be considerate to their personality and identity. Consequently, you should accept when they decline some of your ideas and try to understand why, and let them have alone time if they feel the need to. Don’t try to control everything that happens in their life and back away if they don’t want your help or interference, but keep eye on the matter – you do want to know what is happening with them. Of course, you should request the same treatment of respect from them, too.

39. Do you let external factors influence the relationship?

– External situations or figures can shake up even the most stable relationship if one is not mindful. People you both interact with might choose to interfere and change your minds about each other or your life situation; or something might happen to either of you that will throw you in disarray – a loss of job or a promotion, death of a family member, some other misfortune. If you sense that things between you suddenly start to change, look around for any of the aforementioned factors and try to understand and negate any negative influence they might have on you.

40. Do you accept it when the other person disagrees with your opinions and decisions?

– This goes again for both of you. You can disagree and still have love and respect for the other person. When it’s inevitable to clash your opinions and you have to do something the other doesn’t like, don’t throw around blame and don’t turn it into exchange of insults. If you notice they go there, point it out and try to lower the voice as at this point there is probably some yelling. All in all, keep a cool head and help them to do the same if you can. If you are unable to calm down and listen to each other, it’s likely that things will start to fall apart.

41. Should I try to keep the relationship at all cost?

– If you are asking yourself that, the answer is probably no. Whatever your reason for wanting to quit, it means you don’t have trust in yourself or the other person, and if you cannot resolve whatever is bothering you, then you should let go.

42. How to deal with cheating?

– This is a moment of great heartbreak. If you are the one cheated on, you have to understand what went wrong in your relationship as something must have been lacking. If the pain is too strong to ever forgive and even look at the person in the same way, you would do yourself a favour to get away and work on yourself to be happier in your next relationship; if you are the cheater, again, ask yourself, what lead you to choose another person? You may call it a moment of weakness, but you have to figure out what that weakness was, as it is in the relationship. If you want to be forgiven, you have to solve the issues or else you will cheat again, as the weakness is still there.

43. How to tell the person that you want to break up?

– It’s best to have a face-to-face conversation. Try to be direct and firm and do not give into any excuses you might receive from the other side. Once you’ve reached this point, you will never look at this person the same way as before. Continuing the relationship will be harmful for both, as you will be compromising with yourself; at the same time, you will not be what they are expecting of you.

44. How to heal from a break up?

– Even if you chose to break up, you will need some time to heal from the person you were with. Try to understand how your attitude has changed towards other people and if you’ve developed any defence mechanisms that obstruct your normal socialising; If you were the abandoned one, it’s normal to be hurting – but don’t run to a new partner right away, even if it’s just for comfort. You will need time to be able to access people again and to not enter the trap of toxic relationships. Treat yourself for a while and try to limit your responsibilities for a while, and after the pain starts to fade a little, focus on productive things – a skill you want to improve, a new project you’ve been putting off, fitness or sport, or get a pet to keep as companion and take care of.

45. Why didn’t things work out?

– If you followed all of the above advices, either one of you changed, or they never intended to put in the effort to do as much as you. As people go about handling what life throws at them, they keep developing even as adults. Then, this means change is usually inevitable. It’s possible that one changed faster and the other was stuck at the same spot and didn’t notice – hence, you were no longer compatible. There is no reason for blame or regrets, as this is the natural state of things and all you can do is move on.

46. How to handle regrets?

– Having regrets means that you blame yourself and you have not allowed to give yourself forgiveness. Thinking about what you could have done better will only serve to hurt you more. You have to accept what is in the past and cannot be changed. You can only hope to right any wrongs that are not irreversible, and most importantly, to do better next time.

47. How to trust people?

– Events in your life have led you to anticipate betrayal and you are no longer willing to be vulnerable. You don’t let people get close to you, you question their motives, you are afraid history will repeat itself, you treat them like enemies. How to turn this around? Try opening up to one person – you can look for some evidence that they are sincere and harmless and with no ulterior motives. If you don’t think there are such in your surroundings, try a therapist. No matter how, choose one willing person and start sharing small bits of your mind and feelings in front of them. This can be a reflex and you can train it.

48. How to avoid self-blame?

– Taking responsibility for a situation does not mean you should treat yourself like a criminal and someone that has done something unforgivable. It’s important to understand what part you have to play and what you have control over. Don’t burden yourself with things that you cannot change. Improve the things within your grasp.

49. Should you stay friends with an ex?

–  The short answer is: most likely not. Maybe things didn’t end on a bad note and you still feel them close. And they appear harmless and the reason to fall off was that you just don’t see them that way anymore. All that is fine, however, the fact that they are labelled as “ex” will complicate things in your life as you move on. People react with suspicion when you keep such a person in your life – what if there are unresolved feeling on either side? Are you willing to take the risk of them sabotaging your next relationship? If you don’t cut them off right away, you will have to do so later.

50. What to remember about dating?

– Dating will be a huge part of your life. Therefore, don’t rush just dating anyone. Additionally, work on yourself at any given moment and don’t assume finding the dream date will solve all your problems, because it won’t – in fact, with that mentality, you will likely make an even bigger mess. Enjoy your life and the right person will find their way to you

Author: Kalina G.

References: Based on combination of life experiences and studies in psychology.

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