QUESTION: I just started dating a man who is recently divorced, in his late 40s, and very liberal with his money. I think I might be falling in love with him, but I think I might also be part of his midlife crisis. How do I know if he’s really into me?
CHELSEA SAYS: This is a tricky one, especially because you’re dating a mature man with a recent divorce. He might still have his guard up, which can make it harder for you to figure him out. However, there are still a few telltale signs that he’s seriously into you and that you’re more than just a fling for him.
If your relationship revolves around more than money and sex: You said he’s liberal with his money, which is fine, because he’s probably successful enough and has the money to spend. Fancy, expensive dates are fun, but do you and your older man ever just spend time together without spending money or getting frisky? If you can come home, lounge around, and still enjoy each other’s company, there’s a good chance that your older man is a keeper.
If your man shows an interest in you and your life, like asking how your day was or about your friends and family: Since you’ve just started dating and it’s still early in your relationship, I wouldn’t expect you to start introducing each other to your families, but try bringing up the topic subtly and see how he reacts. If he’s completely against the idea of you meeting his parents, or vice versa, I’d say that’s kind of a red flag.
If he actually wants to spend time with you and shows it by making plans for the two of you instead of waiting for you to plan something: This shows that he’s excited about being with you—definitely a good sign that your relationship is on the right track. Also, does he ever randomly call you just for the sake of it? That’s another good sign.
If he leans in toward you and maintains eye contact with you: That is a positive sign. Whereas if he crosses his arms or puts his hands in his pockets a lot, he might still be trying to keep his distance. Try and read his body language when you’re together.
If he uses more “us” and “we” than “my” or “I” when he’s talking about future plans: That shows that your older man is thinking along the lines of a long-term relationship with you, in which case you’re definitely not part of his midlife crisis.
TRENT SAYS: On the surface, I can see why you might be a little concerned about whether or not your boyfriend is having a midlife crisis. He’s wealthy, recently divorced, and it sounds like you two are going out and having a lot of fun. It’s all fun all the time!
At the same time, you might be putting too much merit into the fact that he’s recently divorced. I don’t know the particulars, but from my experience, the relationship is dead and gone long before the actual divorce goes through. Maybe he moved on emotionally from his ex-wife a year or two (or longer) before the divorce was finalized.
It’s not totally dissimilar to marriage. Sure, you have an actual wedding day, but chances are you feel emotionally, spiritually, and physically connected to the person long before you walk down the aisle. A wedding is a celebration and declaration of your love for each other. A divorce, on the other hand, is a public declaration that the relationship is over.
Anyway, there’s a good chance this isn’t a midlife crisis for him. In fact, this might be the beginning of an amazing relationship. And the best way to figure that out is to give it time to live and breathe. I hate to say it, but men typically aren’t the hardest to read. It’s a cliché, but actions do speak louder than words.
Is he attentive? Does he want to find out all the nuances that make you, well, you? Does he like talking to you and making plans to see you, or are you the one that always makes the first move? And does he rely on money and a bedspring kiss to show you he’s into you?
If you’re keeping an open mind about things, you should be able to tell whether or not he’s really into YOU, or just into hanging out with you.