“I’m Almost 30 and in Love with a Teenager”


I am a 29-year-old woman who has found herself in a serious predicament. For the last four years I have not dated anyone due to how things turned out with the first man I loved. I decided to remain focused on raising my child and going to college to better myself so my son and I would have a more secure life.

I am into gaming, and that is how I met this 18-year-old guy. There was something about him, and I could tell the first time we spoke that he is special. However, he was engaged to be married to another woman who was a year younger than I. Whatever happened between them is none of my concern as I’m concerned now for myself. The things he says to me I have never heard from anyone ever! The way he makes me feel is as if this is the very first time I have ever felt love. Neither of our families want us to be together.

When I followed my heart once before, I ended up single and it took me three years to pull myself together. Taking risks is dangerous now. I know that I have an amazing 4 year old who only deserves the best of me and of life. But talking to this guy makes me feel less alone. He and I have planned to meet in the summer when my life isn’t as complicated. Your thoughts are much appreciated. — Mrs. Robinson

I’m not sure what you’re asking here. But I’m going to assume you want to know whether or not it’s wise to “date” a teenager when you’re pushing 30 and are a single parent of a 4-year-old. And the answer to that is no, it’s not. Even if you knew this guy in real life and he lived close enough to date-date (as opposed to whatever it is you do together online), you’re at completely different stages in life. Maybe in seven or eight years your age difference wouldn’t be such a big deal, but the difference between an 18-year-old guy and a 29-year-old mother is immense. Trying to fit your lives together would be like trying to force a square peg into a round hole.

Beyond that, you don’t sound like you’re emotionally ready to date anyone yet, let alone some teenager you met on a gaming site who lives somewhere else. You talk about your life being complicated, and how taking risks is dangerous, and that it took you three years to get over your last broken heart. And none of that means you don’t deserve happiness or that you’re unlovable or you won’t ever find someone again. But it does sound like you may need to give your search for love a little more time until you aren’t so vulnerable. It seems like the idea of another broken heart is almost more than you can bear, and, if that’s the case, don’t rush things. Continue focusing on your child and yourself. Only date again when the idea of potentially being hurt — which, frankly, is a risk anyone faces when opening herself (or himself) up to love — doesn’t absolutely crush you. Date when you feel strong enough to handle disappointment and rejection. And then, when you’re ready, date locally and date age-appropriately (i.e. someone older than college-age). It’s complicated enough to balance a love life and family life as a single parent. Don’t dump a whole host of other complications on top of that by pursuing romance with someone whose lifestyle isn’t compatible with yours.


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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. Such a smart, compassionate answer! I loved it and agree 100%.

  2. oh sweetie. Don’t do this to yourself. an 18 year old that is online might be not who you think it is. Don’t fall for people online. It is so easy for them to lie to you. Start with dating friends of friends where you have a good referral of reputation. Good luck.

    1. And sometimes it’s not that they’re lying about who they are, but you’re only seeing 1 or 2 parts of them. You don’t really know them, because you only learn about them in that one particular setting.

      1. very, very true. There are so many things you can’t tell about a person just from online interaction.

  3. lets_be_honest says:

    You’re lonely. Get busier, and you will be less lonely hopefully. Even if busier just means something else to do at night instead of gaming.

    1. Great answer! LW, the power of being active and busy is so important. If you have too much time to dwell, it can only hurt you.

      1. lets_be_honest says:

        Yup. I find that with anything that is bothering me, the busier I am, the better I handle it. That might not be great when say, you paint your nails 5 times in a night or clean out your kitchen cabinets at 4 am (cough, cough), but it does really work.

      2. Avatar photo GatorGirl says:

        I’m the same way. When I’m stressed I make my self busier. And somehow that is comforting.

      3. Me three, four and five.

        I find that if I’m worried about something, I have to keep myself busy otherwise I’ll just dwell on it. And not sleep. And it’s a vicious cycle. So, I do things that will keep my mind occupied.

      4. Um…if you ever run out of cabinets to clean…I just want to let you know I’m here for you. I have lots of cabinets. 😉

      5. lets_be_honest says:

        🙂 My girlfriend LOVES when I babysit her baby because I go on a cleaning/organizing binge all night long once the baby is asleep. Her husband has had to call me several times asking where something is. haha.

      6. Um… conveniently I’ll be having a baby soon… haven’t you always wanted to visit Canada? I promise to send you back with all the poutine and ketchup chips your heart desires…

      7. Sorry to threadjack but last week I bought a british guy a poutine. He’d never heard of it before and the concept was so weird to him. He had 2 or 3 bites and didn’t really like it. So I gladly finished it for him. It was just funny to watch somebody look at poutine so curiously!

      8. That’s too funny – Meanwhile back home he loves him some toast with beans and cut up pieces of hotdogs…

      9. Meanwhile my co-workers were trying to convince the poor guy that beavertails are actually tails chopped off beavers.

      10. the british are not known for their quality taste in food 😉

      11. Just had some pountine while I was in Montreal this weekend!

      12. how are you at cabinets?

      13. lets_be_honest says:


      14. Stupid extra N’s!

    2. Or, even if gaming is her absolute pasttime of choice, game as a dude. Change your avatar or character to a male and you won’t get all the weirdness that can sometimes come with being a chick in that enviroment. You can just *ahhhh* play.

    3. Avatar photo sobriquet says:

      I was really stressed out yesterday and so I decided to do yoga, which required me to hang up a bunch of my boyfriend’s laundry to clear out good space on the floor in our bedroom, which turned into a 2 hour deep clean of the bedroom and bathroom. I was too tired to do yoga afterwards, but I wasn’t stressed anymore!

  4. this is a fake, right? right?

    ok, on the off chance it isnt- wendy is right. you are nowhere near ready to be dating… and who uses such dramatic language about getting back into the dating world? seriously, maybe you need to see a therapist, i dont know, but the fact that you are going somewhere where it is so incredibly *easy* to have a non-relationship -met through a game/all interactions already have a root, the game. long distance. huge age difference. romeo/juliet complex. ect- is a red flag for your own life. you need to change that.

    1. Curious why you think this letter is fake? I think we’ve heard waaaay more outlandish letters in the past.

  5. You sound very unhappy. You’re glamorizing the feelings you have for this guy (so special…no one has ever made me feel this way…) and I’m guessing it’s because of your unhappiness. I’m sure many DWers will remind you of your duties to your child, which is only right. But it is also important to consider how you could improve your life so that you’ll feel happier in the long term. It is not by dating an 18-year-old, for sure. This is mostly a fantasy anyway. Try to find out how to feel better about yourself and your life, for your own and for your child’s sake.

  6. “There was something about him, and I could tell the first time we spoke that he is special”
    “The things he says to me I have never heard from anyone ever!”
    “The way he makes me feel is as if this is the very first time I have ever felt love”

    Ugh, ugh, ugh. LW, no. Get it together. I pulled out those^ quotes because maybe, if you see them isolated like that, you’ll realize how over-the-top dramatic & unrealistic you sound. For your own sake, let this entire thing go. Remember how brokenhearted you were from the first relationship that didn’t work out? Feeling this extreme about a person—when there’s nothing even there—is how you’ll end up falling on your face again. Just don’t do this. And yeah, get some therapy.

    Apart from that…HE’S EIGHTEEN. I know he’s legal & all, blah blah blah, but to me, you are basically a predator? He’s a ~kid~. As a 29-year-old woman, you should’ve chuckled & shook your head at his romantic overtures (assuming he’s the one who made them?) before turning him down gently. The fact that you didn’t…that you took all of this seriously (not even going to mention the gaming/virtual/never having met him aspect, ugh)…indicates that something is very wrong with your emotional well-being. I would suggest going to therapy.

    Look, you have a son. Imagine him at 18, talking to a grown 30-year-old woman online. That should unsettle you. Please don’t meet up with this kid at any point. I’m sure you’re lonely—I get that this fantasy is a good distraction from your life as a mother. But you need to find a different distraction IMMEDIATELY.

    1. Oops, I didn’t mean to be all “go to therapy!” at the end of both paragraphs. Usually I don’t suggest it at all, but once would have been enough—sorry.

    2. lets_be_honest says:

      You know, I was feeling sympathetic to this LW because I get what its like to be fairly young and a single mom, but really, you’re right. No 29 year old should be dating an 18 year old. I completely agree.

    3. Didn’t we try to make a rule about sounding like a romance novel =/= actual love or indications of a good relationship? I feel like we should…

  7. Something is fishy. This guy, and when I say guy I mean boy, was engaged once before to someone close to the LW’s age and he’s only 18. Seriously. Something doesn’t add up. This is a bad lifetime movie waiting to happen.

    1. I was thinking this same thing. If this guy is 18 and was engaged to a 28 year old, that means he likely had been dating her for some time before that…which…ew. This guy needs to find some girls his own age.

      1. Sue Jones says:

        Maybe he is from the South where people marry very young, have 3 kids by their mid-20’s and are divorced (the first time) by their late 20’s…..

      2. Well, an 18 year old engaged to another 18 year old is one thing. But this means he was likely dating a woman in her late 20’s when he was still a minor.

      3. Ginger Laine says:


        And that second marriage is to our cousins also. Elementary school sweethearts!


      4. Ginger Laine says:

        That raspberry smiley face is way happier than I intended.

    2. Maybe he just made it up to make the 29 year old he was getting on the hook think he was mature? Even if I was interested in a teenager the fact that he was apparently making a habit of playing with Mrs. Robinson would raise some flags.

      I’m calling BS on the whole thing, he’s probably some 50something perv trolling the internet.

  8. Avatar photo GatorGirl says:

    I say go for it…what’s the worst that could happen?

    1. GG you can’t joke with her…she’ll BELIEVE you…she’ll have another child by the 18 and BGM will just get mad at all women again. It’s too exhausting.

      1. Avatar photo GatorGirl says:

        You’re probably right. So, LW, DON’T DO IT! This is nuts, you ahve a child to worry about.

        Also, how will YOUR life be less complicated in the summer? You’ll still have a child and a boy toy cross country who you’re planning to meet. Want to uncomplicate your life? DUMP the boy toy. Perhaps try online dating in your city. Focus on being a good parent! In side of a game is not a place to met life partners.

  9. LW, you should not meet this guy in person. Doing so is only asking for trouble.

  10. LW: I’m just wondering what this guy has said to you that nobody ever has? I feel like if somebody is saying those types of things whatever they are, that they aren’t really genuine, if they have never actually met you, and can’t see how you go about your daily life. I would take a step back and really think about this situation, because I think it has more to do with you looking for love, rather than you actually falling for an 18 year old who has previously been engaged to a 28 year old (does this not sound creepy to you?) and you only know through an online gaming world. I think Wendy is spot on here, and you really need to take more time for yourself, and clear your mind.

    1. Avatar photo Addie Pray says:

      Let’s make a list of things no one has ever said but if they did I’d be moved to new heights!

      – Ooooh, you have the sexiest love handles, I wanna grab them with my hands and bury my face in them.
      – Just let me make the bed, then I’ll give you a ride to work so you don’t have to walk or ride the bus.
      – You look amazing after Bikram yoga, and you don’t stink at all.
      – I got an idea, let’s wake up early, do you yoga together, then go drink wine, even if it’s only 10 am by then.

      Men, that’s all it takes to win me over.

      1. Avatar photo Addie Pray says:

        ^ I mean, if LW’s 18 year old gamer said those things, then I totally get it.

      2. sarolabelle says:

        I LOVE THIS!

      3. I’ve missed you, Addie. 🙂

      4. Lemongrass says:

        My husband has said the second one! Should I be hiding him from you, Addie?

      5. If I didn’t think my gf would take it as an insult, I’d TOTALLY say she had the sexiest love handles. She does.

        But she wouldn’t take it well.

      6. Avatar photo Addie Pray says:

        Next time call them “voluptuous love handles.” I want someone to call mine that.

      7. Well this should make it easier for Budj now that he is back!

        – oh my that one patch of awkwardly shaped hair on your back is just turning me on, can I run my boobs through it all night.
        – No you don’t ever have to watch the notebook
        – Would you like me to hold it for you, and do all of the aiming so you can read a magazine while peeing too?

      8. I only hold it in the morning’s when it would hit me in my face. I also have to stand like two feet away leaning against the wall to get the right angle…

        And I absolutely agree that this guy is ‘fluffing’ this LW up (i.e. not genuine…)

        An 18 year old has about a 0.2% chance of being responsible / at a point in his life to handle the situation the LW is in.

      9. definitely done the last two on your list, well except go for a run together instead of yoga. I think it is a pretty attainable list, and you will get all of those, well except maybe the love handles part, even though budj…opps I mean the guy is going to love your love handles he isn’t going to tell you that.

      10. Avatar photo Addie Pray says:

        I like to set reasonable goals, so I can reach them.

      11. I’m allll about the second one. Also, someone that makes coffee before you wake up so that it’s ready when do. My fiancee does this on weekends and sometimes I sleep longer than necessary just to have bedside coffee!! (note: I do this for him every Monday through Friday)

      12. lets_be_honest says:

        High five to the coffee makers! I’m pretty sure that’s how Peter locked me in for good.

  11. I agree that it’s not so much the difference in years that matters, but the difference in life experience. He’s an 18-year-old guy. His priorities are going to be different than yours. (At least, they should be.) Maybe if he was 30 with a few years of experience under his belt and you were 40, it could work. But at this stage, he’s a kid trying to find his way to adulthood, whereas you need to be focused on giving the best to your child. I feel that you are lonely and probably missing what it feels like to have someone say all those special things to you. But, please, look elsewhere for companionship. The gaming world is a fantasy. Fun, but a fantasy. Try looking in the real world for a real guy who can share your experience. They’re out there, I promise you.

  12. Lemongrass says:

    Grow up. You have your son to look out for and getting involved with an 18 yo who was (is? Did he cheat on her? It kinda sounds like it but you just don’t give a shit if he did. You should care, a lot.) involved with another much older woman. You aren’t ready to be in another relationship and it sounds like you are looking for drama to spice up your life. That is not fair to your son. He needs stability, not for men to come into his life that have the potential for a major train wreck. When you are ready to date, choose someone a little more likely to stick around after he can buy himself alcohol.

    1. SweetPeaG says:

      THIS! Yes, the age difference is a giant problem (I am not saying this type of age gap has never happened and turned into a healthy, loving relationship… anything is possible). But, the major problem I see is that the LW just didn’t seem to give a crap that this guy was sweet talking her while engaged to someone else. I never understand people that can be okay with that sort of thing. You think he will somehow be honest & faithful to you!? Give me a break! That part of her letter annoyed the hell out of me.

  13. fast eddie says:

    A couple that we’re very close to got married when he was 30 and she was 40 with 2 kids and they’re still together and happy after 25 years so it isn’t your age difference but his youth that could cause problems. He’s just started exploring life as an adult. Remember what you were like at his age. If you go through with the relationship you’ll be playing a dual role of lover and parental figure. You said your life is already complicated with being mother, student and job. Any romantic relationship or adventure will make it more so adding his youth to the mix. I expect that it would quickly morph into you having a second “child” that’s going through puberty. Some aspects of that would be loads of fun and tons of effort to keep the whole thing in harmony. If you have enough energy to handle all that and keep your sanity give it a shot. On the practical side of it I doubt that he can be a financial contributor which adds more responsibility to yourself.

    1. I think if both people are over 30 then an big age gap isn’t a big deal. The maturity differences between 30 and 50 seem a lot less than the differences between 20 and 30 even though it’s only half the age difference. There’s just still so much growing up happening for most people in their 20’s. And this kid in the letter hasn’t even hit 20 yet!

      LW, starting about 7 yrs ago and for the rest of your life, if somone’s age ends in TEEN, that person is not an appropriate potential romantic partner for you.

  14. Sue Jones says:

    LW, It sounds like you are lonely and a bit isolated with all of your responsibilities taking care of a 4 year old all on your own, working, etc. and that this 18 year old reminds you of a time in your life when you had less responsibility and more freedom, which you do not have now (and won’t for quite a long time, since raising kids is a 20+ year project these days). And, again, you are lonely. See it for what he is and what he really has to offer you – a friendship and a respite from your responsibilities through the gaming world. But he is not husband, long term partner material. You need a mensch/equal partner in your life if you are going to partner up at this stage of your life. Not a schoolkid whose mother still probably does his laundry and makes his breakfast. It is up to you whether you decide to change your perspective and keep the friendship for what it is , but don’t go expecting your “soulmate” in this guy. He is a child. And you already have a child.

    That said, let’s talk about the loneliness and isolation that raising a small child can involve. Especially raising it yourself. I got on FB when my son was 4. (and I am happily married). I had by that time been working, raising a small child, home every night while my husband worked evenings, not getting much sleep, having to deprive myself of a lot of little luxuries that I had grown accustomed to because I had to pay for his preschool so I could work (that is another story also!) etc. etc. A vacation for me at that time would have been 30 minutes alone in the bathtub with a good magazine with NO interruption (Mommy? Mommy? Mommy? Mommy?) So I spent every evening after he was asleep (if I did not myself also fall asleep passed out exhausted next to him) on FB friending every last person I ever knew and having inane conversations until my husband came home around 10PM or so…. because I was lonely and isolated. THAT is a common experience for mothers, married or not, of young children. I think the first place to look is perhaps how to build a community for yourself to bridge that isolation, so that you don’t go forming inappropriate attachments to 18 year old boys to assuage your loneliness. I joined a singing group. I made sure I got out a little more to cultural events. One time I even flew to Seattle to see old friends and so I could sleep for a weekend. Look, the truth is , you are LONELY and ISOLATED like almost every other mom of a young child out there. That makes you vulnerable. See that reality and then perhaps you can see this inappropriate attachment for what it is. The truth will set you free. And for the record, THERE IS NO SUCH THING AS A SOULMATE!

    1. This is dead on! I totally agree. Especially about him reminding her about her carefree days.

  15. GertietheDino says:

    My question is – was he “gamer engaged” you know, never having met but acted like it and said they were engaged? And how do you know he is acually 18, he could be some 15 year old on a power trip – which makes it even creepier. Honey, get some therapy, join some groups. Hang out with people your own age (this advice is for him too)

    1. Or he could be a 50-year old looking for a younger woman.

  16. When you were having your child, Casanova was 14. Doesn’t that make you pause? The bottom line is that a ten years age difference is something that can work – but not when one party is 18. And not when all you have to go on is sweet nothings that mean a-b-s-o-l-u-t-e-l-y nothing. Nothing. You haven’t even laid eyes on him…there are so many things wrong here. But I think what comes across is that you are lonely and starved for attention…if you are willing to even entertain this young man’s attentions. Expand your network – get out into the world where you can meet adults and develop friendships.

    My dear – he is just too young, you already have one man to raise. Concentrate on that one.

  17. Avatar photo bittergaymark says:

    Oh please. Grow up already. Frankly, people who allow themselves to be so absurdly emotionally shattered by one lousy relationship should probably give up on them for a good long while (if not forever.) Newsflash: you are about as ready to date as I am to fly to the moon solo in a paper airplane.

    1. ack! I love this! I kind of want to send this to an ex of mine who won’t stop sending me melodramatic emails about our relationship of three months that ended 8 months ago.

      I don’t understand the melodrama.

  18. I’ve been trying to think of something interesting to say about this, but I can’t. He’s too young for you. You’re putting too much weight on what a person says to you on the internet (or phone, whatever). You’re creating this person in your head based on words on a screen that is probably far from who he really is. You obviously already have problems having a healthy relationship, and this is a clear sign that those problems still exist. I’d say this is a bad idea for most people, but especially a single mom. You should be looking for more in a person than “says nice things” and “plays games with me.” Things like that they are responsible, in a similar place in life, want their lives to go in a similar direction, would be good with your child. An 18-year-old boy is likely none of those things. (Responsible, maybe, but likely in a whole different way than you need him to be.) Stop talking to him and try to figure out how to stop making awful decisions.

  19. landygirl says:

    LW, please go to therapy because frankly, it would do you good. In the meantime, dump the teenager and focus on your child because you don’t really need another child.

  20. You have GOT to be kidding me.

    First of all, 18-year-old boys are just that…boys. You have a CHILD to worry about. You shouldn’t even consider meeting this guy. So much can — and will — go wrong. He is still a child himself.

    You need to grow up, get your mind out of your computer game, and focus on real life. Focus your energy on raising your son so he becomes the best man he can be.

  21. LW- I understand loneliness. I am a single mom too. And it is very very lonely. But, you have to get your head out of your ass and think of your kiddo. An online relationship with an 18 year old is not something to sacrifice how far you have come for. A) HAVE YOU SEEN CATFISH?????? B) If you are really serious about dating, ask some friends if they know anyone, go to some parental things at a local parenting group

    Don’t equate being lonely as the end of the world. There are much worse things than being single and lonely. Getting caught on “To catch a predator” is one of them.

    1. “Don’t equate being lonely as the end of the world. There are much worse things than being single and lonely. Getting caught on “To catch a predator” is one of them.”

      Spot on @Beth!! Couldn’t agree more, I could add more but it would just be piling on at this point…

  22. Mrs. Robinson says:

    I would like to thank everyone for the comments and their opinions especially you miss Wendy. However I do not appreciate the comments about going to therapy I don’t need therapy, I did not say that I was in love with a 14 year old or 10 year old or any other small child. I’m in love with an 18 year old, who has been labeled by society as an adult… The reality is that some of what you guys have said is true I don’t know where we will be headed or what the future has in store for us because he is so young. I’m going to give him a chance- even though he is young doesnt it mean that he’s not ready. I may not be ready to start a relationship but it could’ve been anybody but it was particularly him. And to make a correction he was not engaged he was dating a chick who was engaged and he met me. Loneliness is something I really don’t have time for however, I will admit that his kinds words have opened my heart. I want to give him a chance mainly for that reason. Again thanks for the advice! I will take it to the head. Will update in a few weeks as we have decided to meet now instead of waiting.

    1. Avatar photo sobriquet says:

      Why did you even write to Wendy? What advice, exactly, are you going to “take to the head”? Because every single person on this thread has advised you not to pursue a relationship with this kid…

      1. Also, that’s not even the correct usage of “take it to the head.” LW, if you want to date an 18-year-old, you need to work on your slang.

      2. Of all the comments to make, I am ROFL with that one Fabelle!

        Mrs. Robinson has so much to learn from the kids these days…

    2. I don’t understand. How do you mix up someone being engaged and not being engaged? Perhaps if you’re making a bunch of stuff up?

    3. Are you serious? Really, you were not open to anything we said. Why did you even write in?

      “Loneliness is something I don’t have time for”? What does that even mean?

      1. ““Loneliness is something I don’t have time for”? What does that even mean?”

        Here for ya bethany, if I may translate it means “i’m desperate and never fully matured as an adult and rather than grow as a person, take care of my child and take the responsible counseling in therapy that I clearly need anytime it takes a grown woman 3 years to get over a relationship… I just want to hang out with kids online who think I am cool.”

      2. lets_be_honest says:

        I need therapy since as I read your comment, I thought to myself ‘gee LBH, you’re not even cool enough for kids online to think you are cool.’

    4. Avatar photo GatorGirl says:

      Wait…so you clarrified to say “make a correction he was not engaged he was dating a chick who was engaged and he met me”…So, when you met your BF he was dating a girl who was engaged to someone else? WHAT? RED FLAG.

      Look, I personally could careless about your age difference. I care about your kid. Seriously, is this the best choice for him? Really truly is an individual only 14 years older than your child the best person to be a father figure for him? Someone who can not even use correct grammer and spelling and may or may not still be in high school? You need to put your own feelings aside and put your kid first. No, you don’t have to be miserable and lonely, but you can’t take wild chances when you have someone elses life in your hands.

      1. Avatar photo bittergaymark says:

        You can lead a lost soul to logic but you can’t make it think…

      2. Mrs. Robinson says:

        First chance I take in so long and I pick someone 11 years younger than me. So, I am stupid. That’s just it though. Its just one chance, just to see what will happen. I suppose you never took any chances in your life?

      3. lets_be_honest says:

        You shouldn’t take chances that big when you have a child. End of story.

      4. Avatar photo bittergaymark says:

        Hah! I’ve taken nothing but chances all my life and am now a fucking mess. Learn from my example. But — even as dumb as most of my decisions have proven to be — even I never fell in love with the fantasy of somebody who is barely out of high school. (If he even IS out of high school.) And I’ve never had a four year old that I really SHOULD be focusing instead. You’ve never even MET this person in real life — and claim to be in love? Sorry, that is just NOT mentally sound. Frankly, it’s so fucked up, it’s INSANE. Newsflash — you’re not Demi Moore. (By the way, how did THAT turn out, eh? Oh right, he dumped her and she had to be fucking hospitalized…) Wake. The Fuck. Up…

      5. There’s taking chances, and then there’s voluntarily setting yourself on fire.
        For Fucks Sake… the fact that you are justifying being interested in a teenager because society has said he can vote and embracing being Mrs. Robinson is disgusting.

      6. lets_be_honest says:

        Good call on embracing the name. LW, would you like your son to grow up and date a 29 y/o single mom when he’s 18?

      7. Avatar photo bittergaymark says:

        But the name is actually a misnomer. MRS ROBINSON never truly wanted to LOVE Benjamin. Just bang him…

      8. TRUE!!! And in this case if the LW just wanted to get her rocks off with an 18 year old dick I might have different advice… but they are in LOVE despite never meeting, so it’s a shitshow regardless of the ages. She’s just theoretically old enough to know better and a parent which is why we can’t give her the ol’ your just in your early twenties being a free spirit pass.

      9. and the fact that you may or may not have notified the teen to also read through the internet as we all justifiably question your judgment and attempt to point out some flaws in your reasoning is even more disturbing. I hope you are a troll, if not I hope your child has someone else out there to take care of them because you aren’t getting it.

      10. low hanging fruit honey. Really low.

      11. You cannot play recklessly when you have a child. As a single mom, I would love to be able to date around and date stupidly and fall in love – BUT my child, their safety, and their innocence is more important.

        Kid comes first. End of story.

      12. This might be the best thing you’ve ever written.

      13. Holy shit, holy shit, holy shit. And do you see that the guy commented?? Everyone loooook, like 2 comments below.

      14. lets_be_honest says:


      15. This can’t be for real anymore with both of them commenting, can it???

      16. I don’t care, this is going to be good i hope.

      17. I call BS on the kid commenting – She wouldn’t send the link to him…would she? Then again she said he wasn’t engaged to the other 28 year old woman – just dating her when she was engaged to someone else….though the letter says “However, he was engaged to be married to another woman who was a year younger than I”

        so who knows what is true anymore…

      18. Yeah this is some definite trollage going on here!

    5. You are clearly lying, because neither of these are typos, and you don’t make those types of mistakes.

      “However, he was engaged to be married to another woman who was a year younger than I. Whatever happened between them is none of my concern as I’m concerned now for myself”

      “And to make a correction he was not engaged he was dating a chick who was engaged and he met me.”

      1. FancyPants says:

        I love having reading comprehension. High five!

    6. He lied to you about dating a girl one year younger than you, who was engaged to try to pretend he was mature enough to date you. This boy is going to get some, and come back and high five his friends.
      Also do you think that it is a good choice to go out with somebody who was dating somebody who was already engaged, and then met you while he was dating her, and really did not care about all of that?
      Sorry to think about who is going to be watching your son all of the time once you start dating this boy, and you are taking him out every where all of the time, and paying for everything.
      I really think you are making the case for therapy with this update, and it should have started 3 years ago.

    7. This is great. I love today.

    8. Being labeled by society as an “adult” does not mean he is an adult. I’ve always been considered as mature for my age but I can’t begin tell you just how much I’ve grown up and how much I’ve learned since I was 18. I now have a very different perspective on life.

      Trust me on this because I’m a teacher so I naturally spend time every day around certain teenage boys — no 18-year-old should date a 29-year-old single mother. He is in a VERY different place in his life than you are. He has just started to discover who he is. I’m guessing he hasn’t even moved out of his parents’ house yet.

      Also, you haven’t even MET this guy. There’s absolutely no way you can tell if you are in love with someone just by emailing, texting, whatever.

      And finally…the fact that you say “Loneliness is something I really don’t have time for however” proves that therapy would be a great option for you. Plain and simple, you are afraid to be alone. It’s time to figure out why. Once you’re comfortable with yourself, THAT’S when it’s time to start dating again.

  23. I’m sorry, but you can’t say you’re in love with someone you’ve never met in person.

  24. I JUST noticed the photo pick. Nice one Wendy. Subtle yet hilarious!

  25. Imthe18yrsoldguy says:

    Why won’t u all give me a chance I’m very responsible guy and I love her. Please comment I will enjoy

    1. lets_be_honest says:

      No way! Really?

      1. lets_be_honest says:

        I say let’s give this guy a chance. I mean, look at how mature he looks in his hoodie with matchin Justin Beiber hair.

      2. Avatar photo bittergaymark says:

        Plus, living at home, he has no bills to pay and thus doesn’t squander much of his money on food and rent! Meaning? He can totally spoil her! Think of the birthday gifts alone… And, remember, he can still get them a table at Chucky Cheese!

      3. Avatar photo bittergaymark says:

        PS — They’ve both written in? Um, yeah. We’re all being PUNKED…

      4. At least we are being punked on a day when I had some free time… and it isn’t wedding related for once!! 🙂

      5. Sue Jones says:

        Yeah, great SNOW DAY entertainment here!

      6. lets_be_honest says:

        Oh boo. I’m afraid you’re correct. I was so hoping this would become a new DW trend.

      7. Agreed. He looks responsible, and like a great father figure.

    2. Avatar photo Addie Pray says:

      Because you were born in the MID 90’s!?! You celebrated NYE 1999 by going to bed at 8 pm with plastic sheets on your bed in case you peed your buzz light year undies. That is why!

      1. Avatar photo Addie Pray says:

        More reasons:

        – because the LW used to babysit kids the same age as kids who babysat YOU.
        – because you (likely) have not even voted in a presidential election yet, and LW has in… 3?
        – because you’re YOUNGER than justin bieber.
        – because you’re in high school.
        – because you wrote “u” instead of “you” above.

      2. Sue Jones says:

        Because you are 3 (3!) years younger than my stepson who is too young to be dating a 29 year old woman! With a kid!

    3. OK, I’ll play… What makes your responsible? What makes her any different from the other lady you were supposedly engaged to?? Where do you live? What skills do you have? What besides love to you have to offer a small child who is only 14 years younger than you?

      What a shit show… humanity is crying somewhere.

    4. You’ve got to be fucking kidding me?
      REALLY PEOPLE?!?!?

    5. Avatar photo GatorGirl says:

      So you’re ready to raise a young child? Ready to support a family? Use full words and punctuation?

      Look, my brother is a year younger than you. He spends his days riding his dirt bike, playing video games, eating too much pizza, working part time, going to high school. If you persue this relationship (and keep it going for a year or two) your days are going to be full of snotty noses, potty training, budgeting to afford to pay for a family of three, kindergarden, early bedtimes because children wake up early, etc. Do you want that?

      1. OMFG!!! i have to go to classes right now… can’t wait to read how this all mess goes

    6. Fake. No way this guy figured out how to upload an avatar.

      1. Avatar photo Addie Pray says:

        good point! it took me like 10 months.

  26. Another letter where I just have to NOL. (Noping out loud).

  27. Avatar photo sobriquet says:

    When I was 21, I dated a 19 year old for a hot second. He was over-the-top romantic, completely sexy and I was infatuated for about 3 weeks. Then the reality hit that he was just so YOUNG and I bolted. And we only had a 2 year age difference…

    LW, get a grip. You’re so terrified of heartbreak that you’re setting yourself up for failure with someone you know you can never be with. It’s kind of like when students choose not to study for a test so that they have an excuse for getting a bad grade. Dating a man in his 30’s who could actually help raise your daughter… that would crush you if it didn’t work out. “Dating” an 18 year old gamer you’ve never met… not so much. Therapy, indeed.

  28. LW, I think most of us understand having our heart broken. And maybe some of us have needed a good long time to recover, I know I have. But think about it. Really think. Maybe you’re flattered that he says pretty things to you. I bet it’s nice to hear. But. But, do you really want to risk having your heart broken again by someone so completely inapropriate? By someone that will have everyone asking “What were you thinking?” Because it sounds to me like you might be putting too much at stake for a guy who’s essentially a child. What does he know about grown up love beyond pretty words from movies? My husband doesn’t say pretty things. He doesn’t wax poetic about me or our special love (sorry, I had to). But he’s solid and there’s no doubt he’s it for me. Wouldn’t you rather feel that than hear empty, pretty words? Back off, back out, and find someone else.

    1. To clarify, in case my husband ever sees this. He says he loves me, he tells me I’m pretty, but he does not compare my eyes to stars or any crap like that. I just mean I’d rather feel loved than hear it if it doesn’t mean anything.

      1. Sue Jones says:

        If my husband compared my eyes to stars, I would wonder if he felt OK, what really bad thing just happened, or what exactly he was buttering me up for!

  29. lets_be_honest says:

    I’ve had some bad days here on DW, but I have to say this takes the cake. First euphoria about the LW’s boy toy writing in, and then it turning out to be fake. 🙁

    1. Yeah this went from being the best DW day ever to the worst! I was so excited to see the LW’s response, but there is way to much though put into this for it to be real.

    2. Avatar photo GatorGirl says:

      Is it fake for sure? 🙁

      1. Avatar photo bittergaymark says:

        I knew it was fake the minute I saw that hilariously over-the-top dopey picture… But it was fun to (briefly) play along.

      2. Avatar photo GatorGirl says:

        Oh but soo sooooo many kids look like that these days!! Like all most all of my 17 year old brothers friends FB pictures are similar to that one. Sadly that is what a “cool” dude looks like these days.

      3. Yes and doesn’t it strike you as a throw-back to the early 90s (BGM? Anyone else who was in high school then?)

        It’s totally reminiscent of the “skater” look. Then again, maybe men’s fashion just doesn’t change that much from decade to decade.

      4. Avatar photo bittergaymark says:

        Jess! The look — sadly, tragically — is BACK!!!

      5. Mark, did it ever leave?! haha. I used to LOVE the skater boys. In the end I settled for a man with closely cropped curls. And, if I may brag, he looks a lot like Ryan Phillipe.

        Back to the skater 90s thing…This is not the perfect hair example but… do you remember this gem?!!! http://www.imdb.com/title/tt0097438/

      6. Avatar photo bittergaymark says:

        Oh, I get the look is presently all the rage. (Sadly.Tragically! No longer can I lust inappropriately after teenagers as suddenly they all look so fucking stupid! Oh, the humanity…) Still, it was just too ON THE NOSE. Also, his sign off? “Please comment I will enjoy” — talk about an obvious troll…

      7. I think so. A classic troll move is to post something, and then dissapear for a long time so people get pissed off, and then come back, and post another comment, and do the same thing.

      8. How do we know it’s fake?!

    3. I’m so upset they didn’t play along for longer. I was looking forward to them trying to convince us of how real they were

  30. Plus the sex will be horrible. Get off the stupid gaming sites and go where grownup adult mature men hang out. Get laid proper, learn to date like an adult, think about what you want in a partner, then go find him. And as the Sweet Potato Queens say… “be particular.”

    1. Avatar photo bittergaymark says:

      Actually, I’ve had sex with LOTS of 18 year olds…. (RELAX, I was 19 to 20 at the time) And I have to disagree. The sex was always fabulous. Then again — I’ve always suspected that gay guys are naturally just better in bed. 😉

      1. Sue Jones says:

        Or you just weren’t as particular about technique at that age – at that age it is like “WOW!!!!! Pinch me! I am actually having SEX!!!! I am actually really really having SEX!!!!” WOOOOOOOOOOOOOOO!!!!!!!!!”

    1. Avatar photo GatorGirl says:

      Hahaha. That is great. We’ve gotten 3 RSVPs already and just sent the invites on Saturday!

  31. Mrs. Robinson says:

    The last I’ll say is this, there’s no reason for anyone to be upset. It leaves me uneasy that some of you think my life is fake. I have already thought every thought every single one of you have written. I truly had no idea that people would have such a hard time with it. I suppose I was looking for just one person who has ACTUALLY been in my shoes and was willing to comment, I think I read one. I told my guy about this post and he wrote on here when I said please dont. Words can have meaning if there is purpose behind them. I understand what many of you are trying to explain to me and have gathered the main point being “I shouldn’t date him because he is too young”. The reason I even mentioned my child into the equation is because I have never brought a guy around and said “here’s my dude” never once. My child will be fine because i alone care and love him. I’ve been talking to my guy for 9 months and when we meet I’m not sure what will happen? I am trying to remain open minded or dare I say optimistic.

    1. You really don’t make any sense.

    2. Avatar photo GatorGirl says:

      So you wrote in looking for validation?

      Even if “you alone” care for your child, if you have a relationship with this person he will be a factor in your child’s life. End of story.

    3. I think you might have been too quick in dismissing the advice to get therapy… And I’m not even being facetious when I say so.
      The reason you are hard pressed to find someone who has been in your shoes is that wanting a relationship with an 18year old you have never met, who cannot even string a series of words together in a comprehensive way, while you are 29 and a mother of a small child is clearly a mistake. It’s like someone writing in to ask should they walk naked into a police station and start waving a gun around. The answer is no. It won’t end well. That is the only answer a reasonable person can give. So LW – no, 29 year old you with a child doesn’t start a relationship with a 18 year old you ‘met’ online – it won’t end well. And normally people wouldn’t care if you break your heart again but you have a child and I bet he cares if his mother is depressed over some 18 year old she should never have been involved with in the first place. It took you three years to get over your last relationship. How many of your son’s years are you willing to risk over a stranger on the internet? How about you be optimistic about his future a little instead of some ridiculous school girl fantasy you are engaging in? The vast majority of commenters on this site are genuine and honest in their responses to letter writers – and we disagree all the time – but what does it tell you that you have managed to inspire universal consensus in what we have told you? You, at least, aren’t 18. Surely you know the voice of reason when you hear it – hell when you hear it in stereo. I still hope that this is secretly some elaborate ploy and there really isn’t a four year at the center of your manufactured drama. Because how sad for that little boy.

    4. oh, wow, no, you have this all wrong.

      this has nothing to do with the boy you are trying to date. while that is an issue for sure, and fucked up for sure, this is about YOU. this is about the fact that a 29 year old woman with a fucking child believes that 50 shades of grey is an acceptable model of relationships. that a 29 year old woman with a child took 3 years to get over a relationship and has done nothing as to figure out why. that a 29 year old woman with a child actually says things like “The things he says to me I have never heard from anyone ever! The way he makes me feel is as if this is the very first time I have ever felt love. Neither of our families want us to be together” and “When I followed my heart once before, I ended up single and it took me three years to pull myself together. Taking risks is dangerous now.” that a 29 year old woman with a son doesnt have the tools or know-how to handle being single. that a 29 year old woman with a son would rather pursue an immature relationship with a barely legal child instead of looking within as to why she would have those urges in the first place.

      this is about YOU. YOU are an issue, LW. and, unless you fix things, YOU will continue to be an issue, for yourself, for every man you date, every person you interact with, and probably most importantly, every situation you encounter with your son. you need to grow up. the fact that you and this 18 year old kid *might* work means that you are at the emotional maturity of a teenager, and it SHOWS. you need to work on YOU.

  32. I really can’t believe I am reading this–that it literally takes 50 people on a thread to (not) convince an almost 30-year-old mother not to date an 18-year-old child. I am 26, married and hoping to have a kid within the next year or so. My husband and I have been taking care of my now-18-year-old brother for 2 years, and I can tell you from first hand experience, 18 is NOT A F@%!ing ADULT. I don’t care if society says he can now drive after 9 pm and buy cigarettes, he is a CHILD! My brother’s main interests are (in order of importance) 1.) his car 2.) My Name is Earl reruns 3.) his part-time job 4.) following me around the house incessantly asking why I didn’t wash his jeans/change his sheets/buy more macaroni and cheese. A teenager is a teenager is a teenager–they are self-centered and immature because they are STILL DEVELOPING. No teenage boy is ready to get involved with a single mom and her child, let alone one who has all the emotional baggage that this LW seems to be carrying. I’m not even going to TOUCH the fact that she has never laid eyes on this kid in real life, and that she met him playing videogames (if you “dont have time for loneliness,” how do you have time for Final Fantasy or Call of Duty or whatever you’re playing???). That is beyond pathetic, and really clarifies for me that she has no idea what real love is–you CANNOT be in love with someone when you have never actually interacted with them in real life. Can you meet someone online and have a successful relationship in real life once you’ve met? Sure. Can you be in a real relationship with someone across the country online never having seen each other face to face like people did in 1999 on AOL when they were in 7th grade? No. That is immature beyond belief, and speaks volumes about where this LW is in her life. It makes me question whether she is even capable of raising this child, especially since she seems about as mature as a teenager in her responses on this thread. I’m disgusted, and I echo the sentiments of others on the thread who have commented they’re sad/worried for the 4 year old boy who is going to be caught in the trainwreck that his mother is going to make out of her personal life and won’t even have the maturity and decency to spare him from.

  33. Xavier Prentiss says:

    This is why the world is the way it is, how is it that we condone anything and everything under the sun you name it if it is something that might have to do with someone of a different creed, color, race, gender, sexual preference, whatever we all rally together to stand up and fight for that poor gay or lesbian or whatever that is so wounded and abused, yet then someone comes out and says im 29 and in love with a 18 year old all of the sudden we all become experts in what is good right and true.. this world is so convoluted and twisted and odd. everyone is an expert on everything and everyone knows what is right and good for everyone else except for themselves. If you like the 18 year old date him.. who cares. At this point you are better off being hurt by an 18 year old and at least walking away with your possessions and hard work than you would be someone your own age only to end up on the streets and pregnant fighting for child support and food stamps. -Leave each to their own and all will see there was nothing worth fighting for in the convoluted state of we.

    1. Mrs. Robinson says:

      I truly love what you wrote!! I suppose this was a valuable lesson of opinion. Some opinions I’ll never forget.

      1. OMG did you meet him yet??

  34. Hi Mrs. Robinson! I just googled for the same topic and found this page and your situation but i don’t know if it is an old post. I am exactly in same position just without a kid but get out from high school relationship that lasted about 10 years. Years that has passed totally in meaningless way. I feel sorry why i did not cut before when i had noticed it has ended. Anyways This guy helped me during this time and i don’t know but i am totally in love with him and he with me. And yes we have about 2 years that talk and see each other every single day. It is all full of love. We have passed most problems with culture differences, race difference, age differences but distance is killing us. We live in different continent and all time refer ” when we will live both” but can’t say when this time will be since for now it is impossible. I really don’t know what to do! I have a big pressure from family to start something and create family since i am 28 age. Should i wait for someone i never met? And when he is suffering that cne do something for now to meet me? Please tell me what you did and i want to know other opinions. Thank you

  35. Uh, no. Its all bad. It ended. the relationship was bad. I’m 35 now and read like 3 lines and i cant believe i was this dumb!like he just got a job 5 months ago and is paying child support….. was i this dumb yea, yea i was!! damn!! long distance relationships are trying and hard. Good luck. Meeting someone your age or older so you on the same level as responsibility is key. You can talk to some one day in and day out and still not know one thing about them till they are in your life face to face. Just one doubt should be enough to lead you in the right direction. Take it from me.. the hardest lessons are learned from the heart and taught/forced on the mind

    1. scott Sevits says:

      it’s time. you did meet him and foolishly got pregnant. I am 53 and have wanted kids all my life. i wish i knew you then because at least I work and pay my bills. sounds like you would have made my fatherhood dream come true. sadly I never meet anyone like you.

  36. Northern Star says:

    So, you got pregnant?

  37. Mrs. Robinson can you give us a detailed update on what went on between you and the 18 year-old? Also this isn’t another troll account right…?

  38. Yall are rude and judgemental as hell. My husband is 20 and I’m 30. He is a loving attentive stepfather and yes he was 18 when we met. It’s not hard or anything bc we are not both in different stages of life. He wanted to settle down. I don’t think you’re being compassionate to this woman. I also was a single mom with a 4 yr old and guess what? 2 yrs later she is his five almost six yr old. Get over yourselves and let people be happy!!!

    1. Write back when that falls apart, because it will.

  39. don’t do it. my ex wife met a 20 year old gaming and moved to live with him. she was 43 st the time and it didn’t work out. to be honest he sounds like a player, you know the guy that knows what and how to say to females to get what he wants. he is also way to young to be a father to your child. lastly you don’t want or need to get pregnant by someone that young whether planned or not. focus on yourself and your son. love will find you when its time.

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