“Can I Make Him Fall in Love With Me?”

I just broke up with a great man whom I was beginning to dream of a future with. We were together for only two months, but we’ve known each other for over a year on an acquaintance basis. We always had lots of fun together. He acted like a boyfriend, with regular texts throughout the week and a standing Friday night sleepover date. We had met and spent time with each other’s friends. I realize it was very early, but it felt like things could go somewhere. For Valentine’s Day, I reserved a nice hotel room for two nights and he happily agreed to spend the weekend with me, our first time spending more than one night together.

We were having a great time on Friday night. We had been to dinner – he paid – and were back in the room, talking and having some drinks. I was feeling really close to him and, with my birthday being next month, I invited him to have dinner with my family. Well, you would have thought I had asked him to give me a kidney. He told me that where he is from meeting parents means that you’re getting married and that we were nowhere near that. (I agree that we were nowhere near marriage and I explained that my parents would not be expecting him to marry me if he ate dinner with them…).

I told him that I wasn’t thinking about marriage, but that I am always thinking about the future. He said he was surprised that I would be thinking anything could ever be serious between us because, at 38, I am eight years older than he is and we have different cultural backgrounds. He also told me that, since his divorce a year ago, his terrible ex (his words) messed his life up for good and he NEVER EVER will be in a serious relationship EVER again because he is broken. But he would love to continue having fun with me, living in the present without thinking about the future, meaning weekly NSA hook-ups. I told him that that kind of relationship would be wasting time for both of us.

My goal is to be in a committed relationship, to spend the rest of my life with one person who loves me as much as I love him, but at my age I’m beginning to think that that will never happen. Wendy, I need to hear that I did the right thing letting go of a man who describes himself as broken, calls his ex-wife terrible names, and blames her for everything. He has some stellar qualities along with the less desirable ones, and I am struggling to keep from texting him to tell him I want to continue on his terms. While I know better, my commitment-seeking brain is telling me that, if I spend enough time with him, he won’t be able to help falling in love with me and we will be together forever. Please help me stay strong! Thank you for any words of wisdom you care to share. — Missing Him

It’s always disappointing when a person you imagined a future with turns out to not be a long-term match for you. But you know what’s worse than investing two months in a relationship you hoped might last forever? Spending a year or two or three or six in that same relationship and seeing it go nowhere. Getting married to that person only to learn later you want different things or he wasn’t the man you thought he was. Wanting a family only to spend your remaining fertile years with a person who has no interest in having kids. These are all much worse scenarios than investing two months in a relationship that doesn’t have a future.

But I know that what you’re most upset about isn’t so much two wasted months, but is rather about seeing the future you imagined for yourself evaporate instantly. But instead of thinking of this as a loss, try to think of it as an opportunity. Rather than waste however much more time you might have wasted with this guy, you now will have the physical, emotional, and psychic space, not to mention the clarity, to pursue other options. Instead of analyzing this man’s behavior and actions, trying to figure out his feelings for you and where you stand, realize that you KNOW where you stand and you KNOW what he wants. What he gave you — 100% honesty in what he’s looking for — was a gift, and I hope you’ll receive it as such, be grateful for it, and move on with the clarity that you are letting go of someone who simply isn’t a romantic match for you.

I can try to convince you that if you stay strong and keep making healthy, empowered choices, eventually you are going to find the right relationship. But the truth is, I’m not a fortune-teller. I don’t know what your future holds. I think you’ll probably find someone, but I don’t know that for sure, and I certainly can’t give you any guarantee for when that might happen. But I can say that if you distract yourself and dilute your focus by trying to persuade someone to love you, you will only prolong your search and demean yourself in the process.

I know you’re looking for inspiration — you want me to share words of wisdom with you that will give you the strength to stay on course. But instead of sharing my own words with you, I’m going to point you to some people who have found strength through advice shared here in the past and let them inspire you with their updates.

This woman wrote in four years ago and recently updated us on how she’s doing, saying:

“Currently, I’m in a relationship with a fantastically supportive man. It feels great to be with someone because I genuinely want to be and not because I’m scared of what will happen if I’m not. Now I know, whatever I’m feeling is ok, and the only thing I can do is listen to it at the moment. When I don’t, I’m doing myself a disservice.”

Here’s another from a woman who, like you, was in her late-30s and who had just broken up with a guy whom she didn’t have a future with but who was worried time was running out for her to find someone else. She wrote in her update:

“I met my husband literally two weeks after ending that relationship. And we’ve been married for two years now. With my hubby, I never had any doubts about our connection. There was attraction and passion, but also an emotional connection and friendship. There was no wondering, no drama — it just worked. And I think that’s the way it should be when you’re with the right person.”

Here’s another update from a woman whose boyfriend suddenly withdrew once her divorce was finalized. She wrote:

“I realized when I read my post that I was afraid to be alone. But, being alone? Suck it up, buttercup… gotta love YOURSELF, before anyone else will! I COME FIRST, no matter what!

All of a sudden it seemed like everything else fell into place. Literally. Work was better. Friendships were better. I had a sense of myself and worked for a purpose. I took time for myself. I was nice to myself for the first time in a long time.

On the love front, I will say my view on love is MUCH, MUCH different. In my post, one of the things I mentioned was that I had been rock climbing with a friend I thought was really fun. I did keep him at arm’s length, but for some reason he just kept coming back. I was honest with him from the get-go. I told him I liked him but didn’t know what that meant. I was coming out of an abusive marriage and a bad relationship, and I wasn’t looking for a trifecta.

So we became friends and it was all very easy. And then one day, maybe three months ago, we were falling asleep on the couch and he told me he loved me. I don’t feel any sense of pressure to be with or stay with this man, other than when I am with him I am happy. I am fully connected to my life and he is a part of it. Not the other way around. He works to be in my life on a daily basis and treats me as an equal, and I work for him the same way. I do feel a deep sense of connectedness and love for him.

Regardless of where we end up, or where I end up, I am so thankful for everyone who responded to my letter and gave me advice. You all gave me the courage to make the decisions I needed to make. And now I have someone in my life I am proud to stand next to, and I can’t wait to see what the next chapter holds.

These are just a sampling of the many updates I’ve received from people who stayed strong in the face of fear and loneliness — who chose to focus on themselves while leaving space for the right person to fit into their lives. Don’t give in to the temptation of filling the void in your life with the wrong match. All that does is suck up your energy and send the message that you aren’t emotionally or physically available for someone else.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Avatar photo kmentothat says:

    Oh man, I so needed to read this. I’m fresh off a terrible break up with my boyfriend of 3 years that I lived with, who I just caught cheating (and I have been cheated on by other before, so it really burned). Thank you Wendy. Seriously.

    1. WHAT?!? You’re awesome and gorgeous and cool and he’s an idiot.

      1. Avatar photo kmentothat says:

        Thanks so much. I feel like I’m still in shock….idiot indeed.

      2. I’m so sorry this is happening. Truly.

    2. Sorry honey that you’re going through that. Grrr.

    3. Avatar photo Raccoon eyes says:

      kmen, that majorly sucks. But, you are awesome and he is definitely not. Just remember that. You deserve better!!

  2. Stay strong, LW. While Wendy shared some words of others who broke it off and found happiness, let me share with you what my grandma said when I asked her what she saw in her husband of 30+ years. She looked at me sadly and said, “Learn from my mistakes.” LW, she wasted three decades with a man she hated because she was scared of being alone. In fact, she was in her mid or late 30s when she married him. Wendy is right when she said to take this as a gift. I’m sure you wouldn’t want that to be your answer one day when someone asks about your marriage.

  3. dinoceros says:

    I know it’s hard, LW. But your brain is deceiving you by trying to imply that if you got this guy, you’d get the things you want. Not only would you not get them, but you’d lose all opportunity to try for them. My stepmother was dating a man for like 10+ years who I guess she wanted to have a future with, except he was not interested in commitment and, I hear, was kind of a jerk. At some point, they broke up in her late 30s or early 40s. Anyway, she married my dad when she was 43 and is one of the happiest people ever. Like I have to stop looking at her Facebook sometimes because she goes on about how cute my dad is. Had she stuck with the other guy, she wouldn’t have gotten together with my dad. Wouldn’t have met him, and he certainly wouldn’t have started getting to know her because she clearly would have been with someone else. So, now she and my dad have been together for like 16 years.
    The other thing is that had she met my dad when they were younger, they also wouldn’t have worked. My dad was kind of a jerk face to my mom, whom he met when he was in his late 20s. After their divorce, he was in a place where he knew who he was and what he wanted. You don’t want to be with someone who isn’t that great, sitting there wondering if you would have found someone better had you just held out longer.

  4. Avatar photo Raccoon eyes says:

    I think it should go without saying that if a guy says to you that you being X number of years older than him is a reason in support of a relationship not working out, you need to run for the hills, like yesterday. Before you hear his sob story about being a broken little bird. Boo Frikkin’ Hoo.

  5. Monkeysmommy says:

    I always know a story isn’t going to end well when a woman has to brag “and he paid for dinner!”, as if that’s a huge accomplishment. I know I am going to get it for this, but paying for dinner is not something this girl does; at least not until we are married and sharing accounts. I don’t even do the “wallet reach” where I pretend I am going to… (Incidentally, I have a friend who does do this move, then gets mad when the guy takes her up on it. Smh… Offer only when you mean it!). Anyway, sorry, LW, I hate you experienced this. It sucks he used your age as an excuse too; after my divorce, I dated (and eventually married) only younger men, so that’s a bullshit line to throw at someone. 30 and 38 aren’t that far apart in the grand scheme. It has only been two monthS, let him go. He won’t come around or fall in love; at least not with you. What could happen is that you watch him leave you for someone is does fall for. That would hurt far worse. And really, I can see his moment of freak out, if you asked him to a dinner a month away, with your parents, after 6-8 weeks of “dating”.

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