Signs He’s Falling In Love

Reading: 8 Signs He’s Falling in Love

Love & Relationships

8 Signs He’s Falling in Love

One dating coach and expert clues us in on how to know he’s into you 

By Andrea McGinty

Falling in love at age 45, or 58, is much different than what we experienced with college love or meeting someone in our 20s. Why? First of all, we have life experience (I don’t use the word baggage!) that has taught us a lot about viewing our lives — and love — from many different angles and through various lenses. Second, for better or worse, our hormones have developed and changed.

Does that mean we can’t experience chemistry? Absolutely not!

Working with many clients in their 40s through 60s, I can tell you that it’s a very different “second act” love. We absolutely, no question, know what we do not want. But, that doesn’t mean we know what we do want.

After a 24-year marriage, and in my mid-50s, I too was vacillating on the whole dating thing. I had a happy life, was loving my career, enjoying raising my two daughters, had family and friends to keep me busy and fulfilled. Then, one day, the love bug bit me. And just like that, I wanted to date. Though I must admit the thought of kissing a man, let alone the thought of intimacy, scared the heck out of me. How out of practice was I? Was I still attractive? For a fairly confident woman, and someone who helps others find love for a living, the doubts surprisingly hit me hard.

But, just as I would advise my own clients, I plunged into online dating with both feet and no expectations. Looking back, I know that was part of the key to success. No expectations. 

After my first two weeks online, I was reassured I still had the ability to carry a conversation and definitely had some charm left. Fast forward two months, and I met a wonderful man from Boston. Oh, that accent! Fast forward to this past Christmas and he gave me a ring. And guess what else I got? Two more wonderful children — what a gift!  

Dating in midlife can be absolutely amazing, and change your life in ways you hoped and in other ways maybe unimaginable, and it starts with having the right attitude. And (ahem) no expectations. But all of us need that little bit of confidence — a clue — that we’re doing something right, and some reassurance that we’re onto something good helps, too. 

Telltale Signs He’s Falling in Love 

  1. He makes you a priority. Now, he doesn’t just say you matter. It’s all about actions. He may have a busy schedule (as you do!), but he always comes through for you. He wants to spend time with you. You are the first personal adult slot he fills. You matter — a lot — and you can feel it, daily. His first personal slot is reserved for his children — whether they are teens or young adults, they will always be the top priority. (As they should be!) Next in line… you!
  2. He starts planning a future. I’m not talking about a ring or a wedding after six dates. Little things are beginning to come up: What are you doing for Thanksgiving? Are you interested in going to an alumni function with him in the spring?  His daughter’s college graduation? All of these say future.
  3. He wants to meet your friends. One of your closest friends is in town next weekend and you ask him if he’d like to join you for dinner. No hesitation. A prompt, “Of course I would!” says a lot.  Why? This is very important to you as this is your BF for the past 30 years and he jumps right on board.
  4. He wants you to meet his friends — and family. OK, this is a total general rule and also depends on logistics and geography. By date #5, you have at least met one of his “people.” Maybe it’s going to a Trivia Night with his friends or seeing some live music with another couple. He wants you to know you fit into his life — plus, wow, you can learn so much about this man who may be falling in love with you (and you, him) by the quality of his friends.  Family — the final frontier. He may have young children that are under 12. We all know this is a tender age where parents have to be cautious and considerate about who their children meet, and who is coming into their lives. Meeting children is a big vote of confidence in your relationship and the degree of seriousness. On the other hand, he may have adult children. This too is an important meet. Why?  They are much more likely to be vocal about your relationship — especially if it was an acrimonious divorce or widowhood. Again, this signifies much more than a casual relationship.
  5. He’s vulnerable and shares with you. Alright-tttty! Aren’t we always on our best behavior the first few dates? But real life is not perfect. He’s had a tough week at work and instead of all smiles and extravagant plans for that evening, he may suggest a night in with takeout and a movie. He tells you he’s exhausted but still wants you near him. That’s vulnerability — and it’s real.
  6. He amazes you with a thoughtful gift. For no reason. It may be a card. It may be a bunch of tulips. It doesn’t have to be extravagant. I rarely take off a little bracelet I was gifted from my now-fiance on our third date. He picked it up on a work trip and it simply meant he was thinking of me.
  7. He communicates. What do I tell my clients ad nauseam? Three things are essential for a long-term relationship: chemistry, communication, common values. Of these musts, communication can sometimes be the most difficult. Studies show that men and women communicate differently. In a strong relationship, he will communicate in real time — his needs, his concerns, his goals — and you need to do the same. In midlife, with many years of relationship experiences behind us, hopefully we have honed this skill and become much better at communicating our needs and wants.
  8. He compliments you. And, it is sincere. Think about how good you feel when he tells you he loves your smile. Or the color blue you’re wearing. A bit different from our college days, when it may have been in real life or on a dorm phone. (Remember those?) Now, it’s much more likely to be via text in the middle of a busy day at work. How fun and satisfying to know he’s thinking about you.

Andrea McGinty founded It’s Just Lunch dating service in 1991 (before online dating was a thing!) and is currently the founder of, which helps singles navigate online dating. She specializes as a dating coach for people in their 40s–70s and has helped 6,000+ couples to marriage. Andrea has been featured on Oprah and The Today Show, and in People, Forbes, The New York Times, and more.

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