45 Clever Ways to Know If A Man Over 50 Likes You

a woman with glasses and a hand on her cheek next to script that says How to Know if a Man Over 50 likes you

As an Amazon affiliate, I may earn from qualifying purchases. Please read our Disclaimer and Privacy Policy.

It can be hard to know if a man over 50 likes you “in that way”. Dating can be a complicated and sometimes overwhelming experience. Some people meet and know almost immediately that they’re a match. 

I’m going to assume that you’ve been dating someone, or you’ve recently met someone, who seems to want more than a friendship. The problem is that you don’t know what his true feelings are. Does he like you, or does he just want you for one thing?

What you’ll get from this post

In this post, I go over 45 clever ways you can know if a man over 50 likes you.

Ultimately, the best way to move forward in any relationship is through honest communication. However, if you’re not quite ready to bluntly ask the question, this post should help give you an idea of what’s happening.

Red Flags & Warning Signs

It’s important to take note of red flags and warning signs right up front. Sadly, there are a lot of men known as “players”. They play the field indiscriminantly and will literally love bomb you into thinking you’re the greatest thing to walk the planet.

And maybe you are! The danger is when the behaviour becomes coercive and abusive.

Beware of Love Bombing

Love bombing is a manipulative behavior sometimes used in relationships, especially in the early stages.

It involves excessive flattery, constant attention, guilt tripping, and pushing for a deep commitment that you’re not ready for.

In the beginning, it may seem nice to receive flowers everyday. It’s possible that you may not even mind frequent texting from this guy. After a while, however, your spidey sences should perk up. 

Read this interesting article published by the Independent and written by Maya Oppenheim: Gaslighting, love bombing, coercive control – what do these terms of abuse mean?

Psychologists offer several strategies for managing and exiting a love bombing situation. For example, it’s important to understand and recognize the red flags. These may include:

  • Excessive flattery
  • Constant attention
  • Rapid escalation of the relationship
  • Receiving an overwhelming number of texts, calls, or messages
  • Insistent on spending all of your time together
  • Suddenly exerts pressure to commit
  • Lavishes expensive gifts or vacations very early in the relationship
  • Emotional manipulation using guilt or emotional pressure 
  • Isolating you from family or friends
  • A dramatic shift from intense affection to coldness or withdrawal
  • Unpredictable actions
  • Wants to know too much about your financial situation

Shhhhh did you hear that? It’s your instincts talking

If, at any time, you start feeling like this is too good to be true, listen to your instincts. If you want to know if a man over 50 likes you, you can start by keeping aware of subtle red flags.

If you think you’re being love bombed, establish clear boundaries and communicate them to ensure that the relationship develops at a comfortable pace. These behaviours might seem as if he likes you in the beginning, but they are clear warning signs to get away.

The problem is that the man may push even harder when you try to set boundaries. Trust your instincts. You are not obligated to go further with the relationship and have every right to walk away.

If it means needing to block communication from him, then do so without guilt.

a man and woman standing together wondering how to know if a man over 50 likes youPin

Age Gap Dating: Pros and Cons

If you’re wondering how to know if a man over 50 likes you, I’m going to assume that you are a younger man or a younger woman.

I’ll cover the specifics of what to look for below, but in the meantime, there are a few things that are important to know.

When it comes to dating, especially with an older man interested in a younger woman, the dynamics can be different compared to relationships between peers. Of course, the same can be said for an older woman dating younger men.

At some point, the relationship may naturally bloom on its own, leaving no doubt between two partners that there is mutual admiration. For people who need more of a verbal acknowledgement, it can get a bit trickier. 

Communication Pros of an Age Gap

The pros of age gap dating typically means that the older partner, often with more life experience, may bring a higher level of emotional maturity to the relationship.

In this case, the person may feel more comfortable simply asking some questions on where the relationship is headed.

There’s also a prioritization of deeper and more meaningful conversation that comes with maturity. 

Communication Cons in an Age Gap

Growing up in different eras can lead to differences in how partners communicate.

The older partner may prefer face-to-face conversations, while the younger partner could lean toward texting or social media communication.

The older person in the relationship may have different long-term goals and aspirations, while the younger partner may still be figuring out their path. 

Whatever the situation, it’s imporant to work out a mutually acceptable of communicating successfully.

How to Overcome Communication Challenges in Age-Gap Relationships

If you’re wondering how to know if a man over 50 likes you, it’s important to take into consideration the differences that make him unique.

Try to clarify expectations so that both partners are clear about how they expect to communicate the important things. 

By recognizing these dynamics and maintaining open, respectful dialogue, couples can bridge the gap and enjoy clear, fulfilling communication.

In other words, instead of wondering how to know if a man over 50 likes you, you could probably just ask! Sometimes, direct, open communication can be a refreshing change!

How to Know if a Man Over 50 Likes You

If you’re still wondering how to know if a man over 50 likes you, but you’re too nervous about asking the question, I’ve put together a list of possibilities. 

The list is NOT inclusive of every scenario, but it does taken into account the different types of love languages.

For example, there are five telltale signs that a man over 50 likes you. I woven them into the list of possibilities below. 

1. Words of Affirmation

This love language involves expressing love through verbal compliments, words of appreciation, encouragement, and kind words. People who value this love language feel most loved when they hear “I love you” or other forms of positive verbal reinforcement.

If you’re relationship hasn’t reached the “I love you” stage, you might notice this particular love language through the thoughtful gestures he does.

2. Acts of Service

This language is about expressing love by doing things for your partner—helping with chores, running errands, or doing anything that makes their life easier.

People who value this love language feel most loved when their partner helps them without being asked. 

If you get the flu and your guy sticks around to make you some hot soup, take your temperature, and maybe even do some errands for you, there’s a pretty good chance he’s a keeper.

Of course, acts of service as a love language isn’t limited to times of ill health. 

A man who uses acts of service as a love language can show that in many ways. For example, he may take time out of his busy schedule to grab you something you need from the grocery store, without needing to be asked! 

3. Physical Contact

A man over 50 may use subtle physical contact to express his interest in a woman in ways that are respectful and mindful of boundaries.

Subtle touches, like a light touch on the arm or a friendly hug, can be significant. Physical contact is a strong indicator of attraction.

​Accidental but repeated brushes of the hand or arm might be another quiet way he’s trying to establish physical closeness with you, without trying to make you feel uncomfortable. He may use playfut gestures, a friendly nudge, or a light tap to create a sense of fun and fliration.

As always, your common sense or your inner instincts will tell you if the man is just being flirtatious, or if he’s going too far.

4. Quality Time

An older man who wants to spend quality time with you, whether it’s sharing a meal or engaging in activities together, is showing genuine interest.

He may plan thoughtful dates that are tailored to your specific interests, for example, Likewise, he may use the time you have together to engage in deep conversation, listening to what you have to say.

a man and woman running and the woman is wondering how to know if a man over 50 likes youPin

5. Eye Contact

Frequent and meaningful eye contact is one of the most common signs of attraction. If he maintains eye contact during conversations, he likely likes you.

You might notice he tries to maintain eye contact with you, but blushes and looks away quickly. That could be a sign that he is harboring feelings for you.

6. Social Media Interaction

Engaging with your social media posts and sharing things with you online can be a sign of interest. He may also use social media to learn more about your likes and dislikes.

​You might notice that he’s “liking” and “commenting” on your posts more frequently. Rather than just commenting on posts, he might send you direct messages in response to your stories or posts. 

This allows for more private, one-on-one interaction, where he can compliment you, ask questions, or engage in deeper conversations.

In my personal experience, using social media to communicate with each other would likely be more active when you’ve first met someone. 

Over time, when the relationship develops more fully, using social media to flirt may take a backseat to more face-to-face interactions.

7. Initiates Conversations

An older man who makes an effort to initiate conversations and keep them going is showing he values your company and is interested in getting to know you better.

​The first date can be the hardest, because conversations might seem a little forced or awkward as you try to learn more about this person. However, it’s a really good sign if the man listens enough to be able to banter back and forth, asking thoughtful follow-up questions, etc.

​If you’re on a date and you want to know if a man over 50 likes you, listen to him talk. Is he only talking about himself or does he equally contribute to the conversation?

8. Follow-Up Questions

This one is similar to what I mentioned above. Conversation is so important when learning about someone else. People also tend to be on their A-game on that first date. Unfortunately, sometimes men (and women) think of it as a job interview and really want to make sure they jam in every good quality about themselves. 

In that case, they don’t allow a mutual connection to arise. 

If he asks detailed follow-up questions about your life, past relationships, and interests, it’s a good sign he’s genuinely interested in you.

9. Plans Future Dates

Making plans for future dates and activities is a sign he’s interested in building a deeper connection with you. Of course, it’s more than just “I guess we should try this again”.  He should be genuinely excited to meet you again. 

10. Discusses Important Events

If he talks about important events in his life and invites you to be a part of them, it’s a clear indicator of interest. This can be tricky because some of the most important events in his life might not be something he wants to share this early on. 

For example, he may not want to talk about his children or health issues in the begininng. That’s a good thing! It’s normal for conversations on the first few dates to remain on the surface level. 

As the dating evolves, however, he should start to feel more comfortable discussing things that are important to him on a much deeper level.

11. Talks About the Future

Discussing future plans and potential for a committed relationship shows he’s thinking long-term about you. Over time, however, he should be comfortable enough to open up about what he wants for the future. 

It’s a bit of a litmus test to see how you react. He can gauge how likely it is that you’ll be joining him on that journey by your response.

two people hugging each other with bags on their facesPin

12. Receiving Gifts

For some people, thoughtful gifts are the best way to show love. It’s not about materialism, but about the meaning behind the gift. The gesture represents thoughtfulness, care, and attention to what the other person values.

Unfortunately, there can be a dark side to this behavior. If the gifts are lavish and over-the-top from a person you just met, take it as a warning sign. 

​If a man sees a book he knows you want and buys it for you, that’s nice! But if slips tickets to Spain in the book jacket and you’ve only known him 2 days, that could be something else entirely.  See Love Bombing above.

13. Supportive Behavior

Being supportive and showing concern for your well-being, especially during challenging times, indicates he cares deeply. Using platitudes, however, isn’t necessary supportive. He should be asking what you need and what he can do to help, not just saying things like “it could be worse” or “people have survived worse”. 

14. Engages with Your Friends

Any man with an ounce of sense should know that if you’re going to be in his life, he best get on board with your friends too.

He doesn’t have to love all of your friends, but he should be able to see how important they are to you and how they impact your life. 

If he takes an interest in meeting your close friends and family members, it’s a sign he’s serious about getting to know you better.

15. Shares Personal Stories

When he shares personal experiences and insights from his past relationships, it shows he’s opening up to you and values your presence.

Again, this can get a little tricky. If you’re on a first date and he spills all the messy details of a recent divorce, it might be a red flag. 

​If, however, he begins to open up about wonderful past memories and experiences (or not so wonderful experiences) with you, it’s a sign that he trusts you. 

16. Pays Attention to Little Things

Noticing and remembering small details about you, such as your favorite things or past conversations, is a sign of genuine interest. Let’s be real, nobody can remember everything all of the time. But if you’re shopping and he sees the kind of flowers you like in a storefront, he might point it out to you.

He might even buy you the flowers.

This shows that he is learning more about you and wants you to be happy.

17. Respects Your Comfort Zone

An older man who respects your boundaries and comfort zone is showing he’s considerate and values your feelings. Your personal comfort zone can only be defined by you. Therefore, it’s important to set your boundaries early in the dating stage. 

18. Creates Memorable Experiences

If he plans special outings or activities to create memorable experiences together, it’s a sign he enjoys spending time with you. Of course, everyone is different. It’s more about the person’s intention and genuine interest in making you happy.  

Are you still asking yourself how to know if a man over 50 likes you, ask him to do something he might not be comfortable with, like taking a yoga class!

It’s okay if he says no, but if he really likes you and is willing to step out of his comfort zone…that’s a big thing.

Read: 9 Osteo-Friendly Yoga For Couples Over 50

19. Engages in Deep Conversations

Discussing deeper topics and sharing life experiences reflects a desire for a meaningful connection.These deep conversations may not happen in the early stages of dating, but it’s a good that he’s willing to open up to you on a certain level.

20. Shows Appreciation

A man who regularly shows appreciation for the little things you do is expressing his interest and admiration. I also want to say that, in the same way, the man should be able to show patience and respect for the times when maybe there’s been a miscommunication. Nobody is perfect all of the time. The way your man reacts to little slip-ups says a lot about his character.

a man holding a flower next to a woman who is wondering how to know if a man over 50 likes you.Pin

21. Talks About Your Life

An older man who shows interest in your life story and asks about your past, present, and future plans is keen on building a connection. The early dating scene might feel like a bit of a tight rope. You want to share some things about yourself, and you want him to share as well.

22. Shows An Interest In Your Hobbies

If he takes an interest in your hobbies or participates in activities you enjoy, it’s a sign he wants to be part of your world. This is especially true if he is initially uncomfortable, but is willing to take himseout out of his comfort zone for the sake of your wellbeing.

23. Expresses Emotions

An older man who shares his emotions and feelings with you is looking for a deeper connection. What’s really important here, in my opinion, is how he expresses negative emotions like anger.

Based on my own personal experience, here are some things to watch for that could be red flags:

  • he’s an aggressive driver
  • he shouts at other drivers
  • he’s not nice to front-line workers (store clerks, etc.)
  • he openly belittles people
  • he says things about you to other people that embarrass you

Ultimately, a good guy should be able to confidently express his emotions intelligently, not reactively or based in fear.

24. Involves You in His Inner Circle

Introducing you to his close friends and family members is a strong indicator of serious interest. I wouldn’t expect that to happen on the first date! In fact, I might be a little alarmed if that were to happen. However, once it seems like you are settling into a relationship, the next step would be to invite you into his circle.

That said, sometimes there is a good reason for wanting to maintain a degree of separation for a while. If you’re dating a young man, he may have children from a failed marriage that he wants to protect. If you’re dating an older man, he may also have reservations about inviting you into the fold until he’s absolutely sure.

If this becomes an issue, the best thing to do is to talk about it openly.

25. Talks About Shared Values

Discussing shared values and future goals indicates he’s considering a long-term relationship with you. Of course, it’s normally and healthy to have different interests. And if that’s the case, it’s how he respects the things you do that matters more.

26. Creates Opportunities for Alone Time

Making an effort to spend time alone with you, away from distractions, shows he values your company.

27. Is Genuinely Curious About Your Day

Asking about your day and showing genuine curiosity in your daily life is a sign of affection.

28. Compliments Your Achievements

Acknowledging and celebrating your achievements is a way of showing that he values and admires you. A guy who genuinely wants you to thrive is a man with emotional intelligence. It’s a good sign!

29. Supports Your Goals

Supporting your personal and professional goals indicates he’s invested in your future. Let’s say you have a job where you travel a lot. If he can’t accept being away from you during these times, it could be a red flag.

30. Takes Interest in Your Family

Showing interest in your family dynamics and wanting to get to know them reflects his serious intentions. This is another area that can get tricky. No matter how much you love your family….families are families.

The best way to know if a man over 50 like you or not is how much he wants to be liked by your family and friends. He will want to make an effort to show his best self.

a man and woman holding wine glasses and smilingPin

31. Discusses Life Philosophy

Engaging in conversations about life philosophy and values shows he’s looking for a deeper connection. I admit, this sounds a lot like the earlier suggestion on having meaningful conversations.

I would say this is more about sharing each other’s values and what you want from life. I think it’s normal to have a romanticed notion of what your relationship might look like in the future. It’s how you both handle the realities of everyday living that will tell you whether he likes you or not.

32. Shows Patience

An older man who’s patient and willing to take things slow demonstrates respect and genuine interest.

33. Expresses Future Aspirations

Sharing his future aspirations and inviting you to be part of them is a strong sign of commitment.

34. Discusses Relationship Goals

Talking about relationship goals and what he’s looking for in a partner reflects his interest in a serious relationship.

35. Makes Efforts to Resolve Conflicts

If he’s willing to work through conflicts and find solutions, it shows his dedication to the relationship. Disagreements are a normal part of any relationship. It’s how you handle them that can make or break a relationship.

I keep using the phrase “emotional intelligence”, because it really matters a lot. If the man flies into a wild rage, has the equivalent of a temper tantrum, or resorts to belittling you, run for the hills!

36. Introduces You to His Hobbies

Introducing you to his hobbies and interests is a sign he wants to share his world with you. It’s okay if he doesn’t have any straight up hobbies. However, he should be willing to at least talk about something he’s interested in.

Men participate in a wide variety of hobbies including mountain biking, gardening, cooking, baking, sailing, golfing, and much more.

If your man is looking for a hobby to start with you, why not read: 21 Best Bikes for Men Over 60. Keep in mind, that you don’t have to be over 60 for these bike recommendations!

37. Is Attentive to Your Needs

An older man who’s attentive to your needs and wants to make you feel special is showing he cares. For example, if your sick, he might offer to make a meal for you or run some errands on your behalf.

38. Celebrates Milestones Together

Celebrating milestones and achievements together reflects a desire to build a lasting relationship. Of course, by the time you get to this stage of any relationship, you’ve probably already got a pretty good idea that he likes you.

39. Demonstrates Emotional Intelligence

While this may not be a direct indicator that he likes you, it’s definitely a green flag should a relationship develop.

Emotional intelligence doesn’t come easy to some people. It involves a level self-awareness, empathy towards others, are able to self-regulate negative emotions, have good social skills, and is adaptable to change.

40. Shows Appreciation for Your Efforts

Acknowledging and appreciating the efforts you make in the relationship indicates he values you.

41. Is Open About His Feelings

Being open and honest about his feelings and emotions is a sign of a deep connection. You may have to pry those feelings out of him, but if he feels safe in the relationship, he should be willing to open up.

42. Takes Initiative in the Relationship

Taking initiative in planning dates and activities shows he’s invested in making the relationship work.

43. Includes You in His Daily Life

Including you in his daily routines and sharing aspects of his life indicates he’s serious about you.

44. Shows Interest in Your Friends

Showing interest in your friends and social circle is a way of demonstrating he values your connections.

45. Celebrates Your Achievements

Acknowledging and celebrating your achievements, no matter how small, is a sign of genuine admiration.

a woman in an apron painting a vasePin

​​Conclusion

Navigating the dating world with a man over 50 can be exciting and full of new experiences. 

Paying close attention to the subtle signs he’s giving off is one of the easiest ways to tell if he’s truly interested. From his thoughtful actions to his willingness to spend quality time with you, these gestures go beyond being a nice guy—they indicate he might want something more.

If he’s making efforts to secure that second date and you’re both having a lot of fun, that’s a good thing. 

Whether you’re on the same page with your relationship status or exploring different things, it’s important to relax and enjoy the great time you’re having together. After all, a genuine connection with someone who values your time and attention can lead to a fulfilling relationship.

1