Dear Wendy
Dear Wendy

Quickies: “He Has a Girlfriend. Should I Stop Texting Him?”

I recently found an old boyfriend — “John” — on Facebook. We dated twenty-five years ago when I was a teenager and we always had a great connection, but for whatever reason timing never seemed to work out and we parted ways. I had thought about him over the years, many, many times, and tried to find him online but was unsuccessful until a couple of months ago when I found him on Facebook, I sent him a message, and we began texting.

Before I continue, I should tell you that I’m married (not happily) and until recently John lived with his longterm girlfriend. She recently moved out, but they are still in a relationship. He told me that being with me was wonderful and it brought back all of those old feelings we felt so many years ago. We decided to have coffee together and spent four hours talking. We agreed to have coffee the following week, but it never happened. I shared my feelings with him and he said we could not see each other any longer because of our history and because we were both in relationships. I still text him, and he always responds; he says he won’t know for sure what’s going on with his relationship until April when she finds out if she can have children. If she can, he does not want to and their relationship is over.

I am just wondering if he still may have feelings for me. Is this why he no longer wants to see me and is limiting our texting? I asked him if he wanted me to stop texting and he just said that he wanted to keep our conversations to a minimum. We always had a great connection and chemistry, and I would like more. I’m separating from my husband, regardless. Should I stop texting him? — Fanning an Old Flame

Yes, you should stop texting him. John has told you that talking with you brings up the old feelings you shared many years ago, but that doesn’t mean you are meant to be together. In the past, timing was never right, and guess what? It’s not right now either. You’re still married and have not even separated from your husband yet, and he’s with a woman he cares at least enough about that he’s not going to end things with her unless maybe it turns out her desire and ability to have children is greater than his desire not to. And that’s no given. Think about it — if he were really interested in pursuing something with you, he’d break up with his girlfriend. But he’s not doing that. And he’s not telling you to completely stop texting him because he does like you and if things don’t work out with his girlfriend, then he’s got you on the back burner waiting for him. Come on. You’ve got to be, what, about 40 years old? Is this really ok for you? Being unhappily married to one guy and being the back-burner consolation prize for another? I’m thinking no. MOA from them both.

I am an 18-year-old girl and currently seeing a colleague from work who is 42 years old. It started off as sleeping together, and although he never officially ‘asked me out,’ things moved quite quickly into a sort of relationship. He has two daughters (11 and 22) and an ex-wife who lives in Argentina. The fact that one of his daughters is older than I am is something I struggle to get my head around. We joke about how we are both crazy because of the age difference, but he seems okay with it – he has told most of his family and friends about us, including his older daughter. I know they have had mixed reactions, but he has potentially ruined his relationship with his daughter over it (she didn’t react very well), and it scares me that he is essentially willing to choose me over his daughter, even after only a month or so of dating.

I have yet to tell my family, and only a handful of my friends know that we have slept together. He is a good man – he is very kind to me, we have good conversation (although his English is minimal), and his funny personality is coming through more and more each day. I enjoy spending time with him and hearing about his life in Argentina — he speaks with wisdom and knowledge and slight sadness.

I would like to continue seeing him, but only for now; I do not see this as a long-term thing (especially when I plan to travel for three months starting in April). I would feel bad if I ended things now, considering he has gone to all this effort to convince his family we are meant for each other. How bad is the age difference? — The Younger Woman

You say he’s “gone to all this effort to convince his family” you’re meant for each other, but considering that he has potentially ruined his relationship with his older daughter, I’m not so sure he has convinced his family you’re “meant for each other.” And why would he? YOU aren’t convinced you’re meant for each other. This is just a fun little thing for you until you start traveling in April. And you’re going to let him ruin his relationship with his daughter over that? So you guys can have sex and you can feel all grown up listening to his wisdom and knowledge and slight sadness? Get a grip! You are 18 and are in over your head. Let this guy go. Don’t let him ruin his life — or at the very least, his relationship with his daughter — because you like the sound of his accent or whatever. That’s just… well, it’s cruel. And in ten or fifteen years, you’re going to realize just how cruel it really is.

He is not wise. He’s an idiot, blinded by the sparkle of your youth, and though it isn’t fair to expect you to be the one to act like the grown-up here and call things off, that’s exactly what needs to happen. Because at least you know that this relationship has a shelf life, and even if you don’t yet realize the damage he may be doing to his life for a relationship that’s going to end in a few months, there has to be some part of you that feels bad about it or you wouldn’t have written to me. That part of you that feels bad is called your conscience, and it’s a wonderful, and often inconvenient, thing to have. Embrace it and let it guide you to compassionate and wise decisions that, even if not always convenient or fun, keep you from that sinking feeling that you did someone wrong.

Follow along on Facebook, and Instagram.

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

16 comments… add one
  • dinoceros January 15, 2018, 12:38 pm

    LW1: Have some self-respect. I don’t know if he has feelings for you. You guys had coffee once, then he bailed, and then he seemingly only texts you when you text him first. Doesn’t appear to be very interested. Aside from that, he IS interested in his girlfriend, and you’d only have a chance with him if she could have kids — do you really want someone who’s only with you because something went wrong with his first choice? If you plan to run around looking for other men, then get a divorce.

    LW2: You are right to see red flags here. Age differences are fine. But they are less fine when one person is barely an adult. I also agree that it’s a bad sign that he’s willing to ruin his relationship with his daughter for someone he barely knows. Not sure what that says about him, that he’s a bad father, has bad morals, impulsive, whatever, but it’s all bad.

    Do not feel that you are obligated to date him just because he put effort into it. (Also, telling your family and friends isn’t much effort.) He made the choice to do all this — you didn’t ask him to. Don’t stay in a relationship out of guilt. This is a lesson that is good for you to learn now rather than later.

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  • Scarlet A January 15, 2018, 12:44 pm

    LW2, run, do not walk, from an overly-invested 42 year old. So many red flags!

    But Wendy, chill on this “And you’re going to *let him* ruin his relationship with his daughter over that?” LW2 can’t control someone else’s actions.

    This is not something LW2 asked for or wanted, it’s entirely his problem. If HE wants to ruin his relationship with his daughter over a 1 month fling with a teenager, that is on HIM, not LW2. LW2 was legally a child less than a year ago, she certainly does not have the responsibility or ethical obligation to manage a grown-ass man’s life. She does however get to say “Whoa, hold up, this is too fast. I’m outta here.” which is a great idea.

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      Dear Wendy January 15, 2018, 2:20 pm

      Eh, I’m not sure I agree. If I were dating someone I knew I didn’t have a future with and his dating me was ruining his relationship with his daughter, I’d feel an ethical obligation to let him know I didn’t see a future and to end things for the sake of his relationship with his daughter if for no other reason. I think 18 is old enough to start acting like a decent human being.

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      • Scarlet A January 15, 2018, 4:25 pm

        Honestly it just sounds like some prize manipulation on his part. “But I tore up my faaaamily for you!” Who actually does that over an 18 year old they’ve been sleeping with for a couple months? Either a really unstable person or a liar. I agree she should get out, but not because she owes this weirdo (or his family) a damn thing.

    • dinoceros January 15, 2018, 6:51 pm

      The LW herself acknowledged that she’s uncomfortable that he’s ruining his relationship with his daughter, though. It’s not like she’s too naive or too young to understand that it’s problematic.

      Maybe he’s using it for manipulation, but I don’t think it’s unlikely that if he has a daughter older than her that she’s very upset with him.

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    Skyblossom January 15, 2018, 12:52 pm

    LW1 You aren’t available for a relationship. You need to exit your marriage before you begin a new relationship. Ask yourself why you need to find the replacement partner before even leaving the current spouse. If you can’t live alone for a while that is a bad sign about your emotional development. You don’t need a man to take care of you. You don’t need a man to be a valuable woman. You don’t need a man to have someone to talk to and you don’t even need a man to have sex. You will end up in a much healthier, better relationship, if you allow yourself to be alone for a while and if you give yourself the time to be picky about the next man you allow into your life. You will do much better if you aren’t grasping at straws, taking whoever is available, in order to not spend a day alone.

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  • Fyodor January 15, 2018, 1:54 pm

    “We joke about how we are both crazy because of the age difference, but he seems okay with it”

    Yeah, I’ll bet he is.

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  • Fyodor January 15, 2018, 1:55 pm

    “he speaks with wisdom and knowledge and slight sadness.”


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  • LisforLeslie January 15, 2018, 1:59 pm

    LW1 – what is your end game here? If you say “I just want to be friends and reconnect!!” I think you’re lying to yourself. You enjoy the flirting and the flattery – things that you may not be getting from your not-so-good-according-to-you-marriage. You’re draining energy from your marriage. You’re not taking steps to make your marriage better or to move on.

    If you need reassurance that you’re walking away from a bad relationship into a better one, I think you need to re prioritize. Walk away from a bad relationship because it’s a bad relationship.

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  • Another Jen January 15, 2018, 3:11 pm

    LW 2: End it now. It won’t be easier 3 months from now. Creating emotional intimacy and dependence prematurely is a classic sign of controlling behavior. I mean, he’s already informed his family of what? That he’s banging an 18-year-old? That he’s going to marry you? That you’re the one? Did you agree to formalizing your relationship before he announced the situation to his family? I’m guessing you speak Spanish (right?). Because unless you’re actively leading him to believe this is a serious relationship, you have no responsibility for his announcement or the trouble he’s going through. It’s a fling, it’s been fun, but for your sake (and his, assuming he’s not being purposely manipulative and controlling) you should end it now before you end up feeling more obligated for his shitty family relationships and expectations than you already do.


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  • Another Jen January 15, 2018, 3:19 pm

    LW: I can understand how you might sentimentalize the past and reach out to an old boyfriend if you’re struggling in a bad marriage. It makes sense you might want to remind yourself that you’re desirable and there are other options out there. But, if you’re not happy in your marriage, you need to focus on either fixing it or ending it. Flirting around while you’re married is a dead end and a distraction.

    Stop texting him. He’s flattered but has made it very clear that you’re a possible 2nd choice at best…IF his girlfriend decides she’d rather have children more than be with him. That’s less than anyone deserves. It’s not worth dangling on the line for a chance at sloppy seconds while his girlfriend makes up her mind. Figure out what you want as far as your marriage and focus on that.


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  • brise January 15, 2018, 4:57 pm

    LW1: you wonder if this guy has feelings for you: well, it is certainly not the great passion. I don’t understand this need to contact old boyfriends of high school. I wouldn’t be at all interested in going backwards, especially at the high school level.
    LW2: end it before it becomes too messy, not for your convenience when you start your vacation. It will be more complicated for you too if you delay the inevitable.

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  • ron January 15, 2018, 6:28 pm

    LW#1 — Your letter reads like you are unhappy and desperate to escape your marriage, but lack the courage/financial ability to do so without a white knight. To reach decades back in your life to a guy who is in a relationship and already creating distance from you just emphasizes how much you are grasping at straws and how little you are doing to plan a separation/divorce from your husband. Work on yourself and make plans for your future, without this blast from the past — talk to a counselor on your own and also to a lawyer and a financial planner. Decide whether you are willing to live on your own for a while, while reconstructing your life and seeking a new partner, or whether you are willing to put up with your current marriage, because a divorce without a pre-planned next relationship is too frightening for you. What you are doing now is cheating on your husband and any family you have.

    LW#2 — this guy is taking advantage of you. Don’t worry about ruining his life, worry about him ruining yours. Make sure you don’t become pregnant out of this and work hard at not becoming attached to this guy beyond fwb. Yes, the age difference between 18 and 42 is huge and I’m guessing he was getting to know you before you were 18. He’s a predator. The negative reaction from oldest daughter is a natural reaction to discovering her father is a predator. I don’t think many daughters would react well in this situation. She’s probably just counting her blessings that he didn’t molest her and making sure her younger sister is safe.

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  • ishkabibble January 15, 2018, 6:32 pm

    LW1, I’m going to quote your own letter back at you:
    “. . . we always had a great connection, but for whatever reason timing never seemed to work out and we parted ways.”
    The timing still isn’t working out. You’re both in relationships. Nothing has changed. It’s time to leave this guy in the past where he belongs.

    And I would also advise for you to leave your marriage and be alone for at least 6 months; this looks like you’re scared of being alone and trying to line up a new relationship to jump to. It’s okay to be alone! And it’s also really important to have some alone time between relationships. I’m sorry your marriage didn’t work out, but the next relationship will have a much better chance of success if you take a breath to figure out who you are outside of your marriage.

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  • carolann January 16, 2018, 12:21 am

    (After 25 years LW 1 and old boyfriend are completely different. )
    He is trying to be nice and not totally blowing you off…you are coming off as desperate. Plus he probably doesn’t want anything to do with the drama you have going on with your marriage. Don’t embarrass yourself that way. You don’t have to jump from one man to the other. It won’t kill you to be on your own for a while. If you really are planning on leaving your marriage…I hope you step back from your romantic fantasies and give you marriage a second look before giving up. (unless he is abusive, a cheat etc then run like the wind)
    LW2-I think he is trying to manipulate you. Do you know for a fact that he told his whole family about you, or are you just taking his word for it? I call b.s. on this one. You are 18 years old. You should be playing the field with someone closer to your own age. No, age differences aren’t bad when both parties are mature adults. Yes, you are legally an adult, but you haven’t really had much life experience yet and you deserve to grow and learn about relationships before getting involved in something serious.
    I think you should end this quickly, like rip it off like a bandaid.

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  • carolann January 16, 2018, 12:32 am

    p.s. my dad married a woman who was younger than me. (I was 26, I think she was 24) It freaked me out. He brought her to my house. (just showed up uninvited one day) And I wouldn’t even open the door.
    When he died he was married to a woman who was only two or three years older than me. I didn’t care for that either. My dad was married many , many times. He was very good looking, very intelligent, very charismatic and a bit of a player. I felt sorry for his wives…he cheated on every single one of them.
    I myself have had a couple relationships where there was a big age difference…(the biggest was 13 years) but to me anything more than 15 years is too much. If one person is old enough to be the others parent that just grosses me out! Just my opinion.

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