Answering the $1M Question: Is He Into You?

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At least half of all the emails I get from wonderful women who are over 40 and looking for love are about the same question you’ve probably been asking since you were a teenager: “Is he in to me?”

Often the answer is: If you have to ask, he’s probably not.

The other common answer is: No way to know…give him time. So many of us think about the “Is he in to me?” situation way too soon.  After the first date – especially if you were in to him – we’re wondering if he saw the same thing we did. You know…did he feel the Connection?

Most men are different than we are. (Big surprise, right?) They are pretty good staying in the information gathering stage until they see enough evidence that you might be The One. That doesn’t mean they don’t make decisions soon – they do. But the decision may be that he likes you and wants to see you again. Then he can stop there.

What do we do? We decide we like him but then might start listing all the things that are so great about him and might make him a great boyfriend or husband. We replay the date in our heads. We second guess ourselves. Then we make the jump to trying to figure out what he thought and was going to do next.

Rumination is a female art. It’s kinda how our brains work. So when you start going down the rabbit hole, hold tight and try to stay in discovery mode. Keep gathering information. It may turn out you don’t even care if he’s in to you.

Here’s the good news: when he IS in to you, you will know it. This is especially true of men dating over 40. Real grownup men don’t play games. When they are in; they are in.

Here is how it looks when a man likes you:

1)   He keeps showing up.

He calls, texts, emails, and keeps asking you out. He is on time or he calls if he’s a little late. All good signs! Remember though, he has a life. At the beginning, give him a little time between contacts if he needs it. But once he has you on his “maybe she’s a keeper” radar, you won’t be able to get rid of him.

2) He tries to make you happy.

He is thoughtful about your dates, planning something he thinks you will like. Or he is sure to ask you where you want to go. (When he does, thank him and suggest something you love that’s maybe out of the norm. Roller skating? Museum and lunch?) He is nice to your dog, he compliments you and lets you share his dessert. He makes sure are warm enough and your car is safe. These seem like small things but they aren’t. They are big signs letting you know he cares about you. Pay attention to these and when you receive them graciously, watch his eyes light up.

3) He tries to impress you.

This part can be annoying if you don’t understand it.  You may think he’s a bit arrogant, self-absorbed or bragging. (This article talk about this more.) If you can just let him have his moment and know it’s coming from flattery, you might actually find yourself impressed by what he’s telling you. You can smile to yourself because you know this means he wants you to like him. (Men don’t generally try to impress women they don’t care about.) It’s not exactly the way we gals do it, but it is their way and it pays to understand that. And, again, another good sign.

4) He shares with you.

When you are together or talking on the phone he is present, happy and interested – most of the time anyway. (A bad day at work can make anyone grumpy or distracted.) Overall his mood is good when you are together. He asks you how your day was and asks your opinion. He remembers the name of the person in your office you can’t stand, knows what music you like and checks in with how your aging grandmother is doing. He tells you about his day, his plans and, in general, what he’s thinking.

It’s pretty simple. Men are pretty simple. When they like you they show it. With grownup courtship there should be no big mystery to keep you up nights. No secret code in his emails to decipher. No having to read between the lines when you talk.  No going over and over what he really meant. When he likes you, you will know it and feel it!

If you like him, or think you might be in to him, I suggest you just be available, accepting and stay conscious of his actions. Remember, he’s a man and may do things differently than you expect.

The flip side is also simple. When he stops calling, he’s decided. He’s not in to you.  Period.  Even if you think you really like him, you had so much fun together and so much in common, etc.  It takes two to tango and without him the dance ain’t happening.

If you start going down the rabbit hole of worry and doubt, STOP and ask yourself honestly: Am I really that interested in him? Do I even know him? Do I just hope that he is Mr. I Love You so dating is over? Is it you ego that wants it? Be sure you’re not wasting time and energy on a man you really don’t care about.

There is no magic number of dates where one should know. It usually starts more like a simmer than a roaring boil, so it may not feel the same way it did in your 20s. Or, occasionally it could be like my experience where we met and knew pretty darn quickly.

Until you feel it, he feels it, or you go your separate ways, it’s best if you  just live your life and let it be enough that you are both enjoying each other. Besides, isn’t it a relief to just “be” on a date without having to project in to the future, read between the lines and Monday morning quarterback?

This is a key component of dating like a grownup. This is what leads to loving like a grownup, which leads to….well, I think you get my drift. Anyway, it all has to start somewhere and that is at the beginning, which is discovery, self awareness and patience. And when he’s in to you, you’ll see… you won’t have to ask.


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  1. Lori says

    Sorry writing a short story here..So we stopped seeing each other although he messaged me every single day. Now we are dating again but its not the same. I feel like hes holding back and we don’t see each other as much. I just want to get to know him better. See if this relationship could go somewhere. Although I have my doubts. I have never met a man I have so much in common with. We go hiking, kayaking, snowshoeing, and right from the get go things were very comfortable. It’s like we’ve known each other for years. If you will excuse my expression it’s like “friends with benefits”. I’m not in love but I sure am in LIKE…I just don’t want to scare him off. If he backs off again I’m done. Oh and one more thing. He plays video games. We did have a disagreement about that. He said I was trying to change and control him because I said it was rude to play when I’m visiting because he is gaming online talking to a bunch of his online friends via headset and it completely excludes me. He says its a big part of his life and he enjoys it. I don’t want him to give it up…I just don’t want to interfere with our time.

  2. Lori says

    Thanks Bobbi for the info. He was into me..I think. I got a little too demanding and needy. He told me he was not ready for a relationship though so he broke it off after 4 months. After a 3 week ” break” ,during which time we continued to text on a day to day basis, he asked me for a date and told me he cares more then he thought he did, missed me and wanted to resume our relationship. My question now…What should I expect?

    • says

      Expect what you want and need! And if he can’t give it to you, he’s not for you. And check yourself on that “I got too needy” thing. Did you really? Or did you simply express your needs. Two really REALLY different things. You have a right to want to feel a certain way and receive certain things in a relationship. If your expectations are reasonable and real…no excuses or apologies are required. Does that make sense?

      • Lori says

        Hi Bobbie, Thank you. It does make sense. I guess I’m just not sure if my expectations are reasonable. The relationship did move pretty quickly despite our early discussions. We did communicate openly about taking things very slowly as we both had only been separated for a relatively short time, myself about 6 months and him about a year. We were spending A LOT of time together. Every day I had off we spent together. I started to expect to see him on those days. It was kind of a given. I was completely following his lead while getting my needs met as well. It was working or so I thought. Then all of a sudden BANG!! I get the talk.. ” We would be better off as friends and I’m not ready for a relationship.” I told him neither am I. I just want things to continue the way they were.

  3. Innocent Bystander says

    Thanks for the information on how men try to impress us. Usually I’m not impressed by this stuff because it seems self-important or like he’s “trying too hard,” but now I can see that it’s just a different approach!

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