Dear Wendy
Dear Wendy

“I’m Dating An Incarcerated Alcoholic”

I’m an 18 year old college student, and the guy I like just turned 30 last week. We met on an online dating site about a year ago and started out just chatting. We now Skype constantly and see each other as much as possible. He lives about six hours away but has plans to move closer to me so hopefully some day we can move in together and start a real life. He’s currently incarcerated (fell asleep drunk in the wrong apartment). He’s also decided to get help (rehab) for his alcohol use and find the roots of his issues so he can truly be happy. His alcohol consumption has never negatively affected me. The problem is that I haven’t told my parents about him yet. They’re just a couple years apart and are generally quite traditional. I’m really worried about how they will react to our relationship. I know at first there will be some shock. I know that after he gets his problems under control that he can provide for me, and wants to. I truly believe that I would have a safe, happy life with him. Is the age difference really something that could hinder our relationship in the future? What should I do about my parents if they disapprove? — Not Quite Jail Bait

What do you mean your boyfriend’s alcohol consumption has never negatively affected you? He’s in jail because of his alcohol consumption! Doesn’t that negatively affect you? And why are you so sure you would have a “safe, happy life” with this older incarcerated alcoholic who lives six hours away from you and hasn’t yet been rehabbed or “found the roots of his issues so he can truly be happy” anyway? There’s a lot working against the success of your relationship (your age different isn’t even the biggest factor). You must be aware of that on some level or you wouldn’t be writing to me, no matter how deep in denial you currently reside. If you take nothing else from my advice to you, please take this: you should never, ever make long-term plans with someone who doesn’t have his problems “under control” yet. That he’s making plans to find the root of those problems or whatever isn’t enough.

I believe in redemption and I think people can change, but the fact that he isn’t redeemed yet means you should not be envisioning making a life together “some day.” I’m not even going to get into what it means that he “fell asleep drunk in the wrong apartment” and ended up in jail. I mean, if that doesn’t scare the hell out of you already, I’m not sure what I can say that will. But I will say this: be careful.

As for your parents’ potential disapproval, you should listen to them if they voice their concerns and consider whatever arguments they might have. Parents certainly don’t know everything, but they often know a lot, and as long as they’re supporting you in some way, you need to respect what they have to say. In the meantime, live your life. You’re 18. You’re in college. Go out with boys your own age. Socialize with friends. If this guy is so important to you and what you have is so special, it will be there down the line. Hopefully, way, way, way down the line.

42 comments… add one
  • AnitaBath January 27, 2011, 3:14 pm

    I say this as a twenty year old dating a thirty-eight year old man:

    You’re eighteen now and you met on an online dating site about a year ago? That would put your age at seventeen, which is illegal. I know there’s not a huge difference between 17 and 18, but I think it says A LOT about a man’s character when he is willing to pursue an ILLEGAL relationship with a minor that he knows only through an online dating website. Obviously it’s not the age difference I have a problem with, just the skeeviness that this guy is letting off in huge, crashing, tsunami-like waves.

    Perfect advice, Wendy. LW, don’t give this guy a chance until he has his act together. It definitely sounds like he’s feeding you lines.

    Reply Link
    • Amber January 27, 2011, 3:27 pm

      That’s what i thought when I first read this! Just so wrong and so creepy. Definitely time to move on from this guy.

      Reply Link
    • darby January 27, 2011, 3:42 pm

      I don’t believe the relationship is illegal unless it is a sexual one – and even then, different states have different ages of consent. Although this situation has warning signs ALLLLL over it, an illegal relationship is not one of them.

      Reply Link
    • AnitaBath January 27, 2011, 5:51 pm

      Well it’s not illegal to just talk to a seventeen year old, obviously, but if they were on a dating site that suggests that they were looking for someone to become romantically or sexually involved with. The details could be different and I may be wrong, she may be 18 and eleven months and she could have met this guy ten months ago, but if he WAS trying to become romantically and sexually involved with a minor, I think that says a lot about the type of person he is.

      Reply Link
  • cdj0815 January 27, 2011, 3:19 pm

    I really do not know what to say about this particular issue. It makes me uncomfortable on so many levels.

    Reply Link
    • baby.blanka January 28, 2011, 9:22 am

      Right? It was a train wreck from the third sentence! Wendy’s advice is spot on with this one. I am wondering what exactly made the LW come to the conclusion that she could have a drama-addiction free life with him? It might not be fair to do so – but I also kind of wonder about 30 year old men approaching 17 (or 18… or 19) year old girls as well. I have a lot of friends in the 30ish age range and when they see girls that young they might think they are cute or whatever but would never dream of going after them (for a million different reasons, aside from it feeling creepy).

      Reply Link
  • Marie January 27, 2011, 3:19 pm

    Well said, Wendy. That scared me too he “fell asleep in the wrong apartment.” Speaking as someone whom got mixed up with someone similar years ago, yes, listen to your parents, this man I am sure is manipulative, mine gave me some mumbo jumbo about being a Christian and our bodies are our temples and having been raised by two naive parents, I figured out with some good friends help what he was doing. Please run from this guy and yes, date some guys your age and in real life to experience real life. I think these dating websites can be good to meet someone initially but then the idea is the people meet soon after meeting online and continue dating in the real life and get to know each other. Also remember that lots of times people may connect on skype and the internet and when they meet in person they are like oh my god no!

    Reply Link
  • Nuttin January 27, 2011, 3:35 pm

    In AA they say no relationships for at least a year. If he really loves you and you him, it can wait. Give it a year, you owe yourself that at the very least.

    I love the saying you know when an alcoholics lying, when his/her lips are moving, your being lied to. Stop the denial he isn’t that special.
    He’s a drunk with a criminal record.

    If you were my daughter, I would bring you to the nearest jail, rehab facilty and womens batttery shelter to show you your future.

    Reply Link
  • AnitaBath January 27, 2011, 3:40 pm

    This may be presumptuous and ignorant as well, but why is a seventeen year old on a dating website in the first place? I’m not familiar with them, so I don’t know if that’s common, but I wonder if that speaks to a bigger issue that the LW might have.

    Reply Link
    • Laurel January 27, 2011, 4:16 pm

      Agreed. LW, please, socialize with people your own age!

      Reply Link
  • ladiejoy January 27, 2011, 3:42 pm

    Eek!! AB I was hoping you’d weigh in on this one.

    Seriously, chickie… this has problem written ALL over it. First, his story is majorly fishy. Fell asleep drunk in the wrong apartment??? Sounds highly suspect, and I doubt that’s the real story.

    Please tread lightly and take Wendy’s advice on this one. See if you can’t just wait it out until he’s released and he gives you some sort of indication that he’s actually a decent, caring guy with your best interests at heart. If he’s not, run fast & far.

    Reply Link
  • REV January 27, 2011, 3:46 pm

    Ton’s of experience in this department. I used to be your potential boyfriend and let me tell you, your in for a ride. I would have lied to you, stole from you, hurt you emotionally, physically and ruined your way of life. I loved girls young and naive such as yourself. That’s where the age difference comes in. You want to believe in a happy white pickett fence existance. I had robbed at least a 1/2 dozen women of those dreams by the time I was 30.

    Like the previous poster said. “Give it a year, I say five years. If you haven’t heard the expression “how low will you go” you have now. Your now at the bottom of the man pool. Swim out of it, fast.

    Reply Link
  • ape escape January 27, 2011, 3:50 pm

    Oh, my gosh. Run awayyyyy. Far away. There are so many other fish in the sea! And you’ve barely even started fishing! Throw this one back.

    Anita, you took the words right out of my mouth — this dude’s character, or (extreme!) lack thereof, is pretty apparent. And LW says they “see each other as much as possible” — do you seriously drive six hours to visit him in jail? I just – I can’t – I’m freaked. This guy is such bad news and SO not worth your time. I feel like LW needs to think about why she’s settling (at 18) for this guy — is she maybe worried she doesn’t deserve better? Girl. YOU DO. moa!!!

    Reply Link
  • Sarah January 27, 2011, 4:08 pm

    I don’t understand why he is in jail. Anyone understand from the letter?

    Reply Link
    • princesspetticoat January 27, 2011, 8:45 pm

      I was curious about that too. “He fell asleep drunk in the wrong apartment”. It could have been a situation where he got himself into the wrong place at the wrong time… maybe he was found passed out in a drug house?

      Or, maybe he actually passed out in the wrong apartment. As in, walked into someone else’s apartment, but thought it was his apartment, and passed out.

      Reply Link
  • Diana January 27, 2011, 4:10 pm

    oh honey… i’m not knocking the age thing at all, but at YOUR age that IS a big difference. like everyone else has been saying wait a while. go do your own thing, have some major life experiences of your own. he needs to get cleaned up and prove that he can take care of you like you think he can, cause right now all he’s doing is talking. and talking won’t love and support you.

    Reply Link
  • Laurel January 27, 2011, 4:20 pm

    Can anyone explain this part to me:

    “The problem is that I haven’t told my parents about him yet. They’re just a couple years apart and are generally quite traditional.”

    Specifically, the “they’re just a couple years apart”. Does she mean her parents are also close in age to 30? Because if that’s the case we’re also talking some seriously young teenage pregnancy on their part. Which might be another reason they’d be really concerned you are being pursued by such an older man.

    Reply Link
    • Morgan January 27, 2011, 4:51 pm

      I think she means her parents aren’t far apart in age from each other…so they would find the age difference between the letter writer and her boyfriend weird. Because you know, if Dad had been 35 when Mom was 25, they’d have been totally cool with their 18 year old dating a thirty year old man in jail. Not.

      Reply Link
    • applescruff January 27, 2011, 5:11 pm

      I think she means her parents are a couple of years apart from each other in age – meaning they wouldn’t get the dramatic age difference between LW and this guy.

      Reply Link
  • Natasha Kingston January 27, 2011, 4:35 pm


    Reply Link
  • unbounded January 27, 2011, 4:36 pm

    Wow…this poor girl is so out there it makes me wonder if she is even real. She’s so concerned about the age difference that she is blind to the other glaring issues in her relationship!

    Good advice Wendy – I bet this is one of those times that you wish you could reach through the computer screen and give the LW a good hard shake.

    Reply Link
  • Avatar photo

    Skyblossom January 27, 2011, 5:14 pm

    Most people pair up with someone who matches their maturity level. Meaning that this guy may be 30 but his emotional and maturity level is more like 18 if he currently matches you. You’ll continue to grow but he seems to be stuck so in a few years you’ll be 20 and he’ll still act 18. Give it five years and you’ll be 23 and he’ll still be acting 18.

    Give yourself lots of time. If it’s really meant to be it will last and if not you’ll save yourself a lot of heartache. Don’t think about moving in with him until he has straightened himself out. He could spend years getting ready to straighten out or sober up and never do it.

    I don’t know how you think someone who is in jail could take care of you. Finish college and you can take care of yourself.

    Reply Link
  • Eden January 27, 2011, 6:40 pm

    Seriously. Don’t waste your time dealing with adult issues when college is the only time to act like a kid. If you’re boyfriend’s really committed to solving personal issues you and I both know it’d take at least a few years. Meaning, the both of you need space while he takes responsibility for his actions and you map out and journey through college life. Needless to day he had his time in college to have fun in college and if he really loves you your bf will let you do the same. Mean while perhaps some counselling is in order for the girl? There’s no reason for a beautiful, 18 year old to resort to online dating for a match. Seems like you’re desperate for love and now you’re pouring it out onto the wrong guy.
    Good luck!

    Reply Link
  • Delilahgem January 27, 2011, 6:46 pm

    Run fast and far in the opposite direction. My father is an alcoholic and I didn’t have contact with him until I was 25. And that didn’t last very long. My best friend is an alcoholic who has been trying to get and stay sober for five years. It is a long, hard, uphill battle. And at 18, if you have the opportunity to save yourself this kind of heartache, please, please do so. There’s a reason they tell people to stay out of relationships the first year. They’re just not ready or healthy for it. If for some reason it doesn’t work out, they could end up back at square one, or worse. I know others have said this, but I cannot stress enough how manipulative alcoholics are. They can also be quite charming. True wolf in sheep’s clothing. You are so young, you have so much to look forward to, especially in dating. Again, as others have said, if you meet again and this guy truly has his act together, and feelings are still there, then maybe consider it.

    Reply Link
  • kel January 27, 2011, 8:02 pm

    I dated a guy 8 years older than me when I was 18. He ended up becoming an alcoholic and we eventually grew apart when I hit my early twenties. I would say wait and see if he does get his act together and maybe down the line date. Plus when I was 18 I thought I knew everything of what I wanted in a relationship, but I changed too.

    Reply Link
    • Anne (I Go To 11) January 27, 2011, 8:49 pm

      Your last line–exactly! There’s a saying I find to be true more often than not: “When I was 18, my parents didn’t know anything. When I was 21, I was amazed at how much they learned.” I remember being 18 and thinking I had everything figured out. 10 years later, I realize how incredibly naive I was.

      LW, don’t feel like you need to settle for a 30-year-old man that doesn’t have his act together. Definitely MOA!

      Reply Link
  • Dennis Hong January 27, 2011, 8:47 pm

    Dude, give the guy a break. I fall asleep drunk and naked in random people’s apartments in their beds all the time. It’s a curse we narcoleptoholics have to bear. In fact, I’m drunk and asleep right n

    Reply Link
    • Anne (I Go To 11) January 27, 2011, 9:06 pm


      When my husband was working on his bachelor’s degree, he had some crazy drunken escapades. (This was before we met.) One time, he was drunk and trying to find his friend’s apartment. He opened the door, went inside, and fell asleep on the couch. Problem was, it wasn’t his friend’s apartment, it was an apartment that looked and was laid out just like it. Oh, to make matters even better, he was wearing someone else’s hoodie backwards and using a laptop case as a pillow. Luckily, no one saw him, and he was able to sneak out before anyone did. If someone did, and called the police, I doubt he would’ve been incarcerated for it (especially since he doesn’t have a criminal record.) Therefore, I think there’s some serious details being left out with why this guy’s really in jail. Did he have a warrant outstanding? Something’s not adding up. Then again, this whole situation is just all sorts of messed up.

      Reply Link
      • AnitaBath January 27, 2011, 9:28 pm

        I’m thinking that he “accidentally passed out” in an apartment that the cops ended up busting for drugs or some other tomfoolery.

        You know, like how the marijuana that’s always found in the cars in COPS is never the driver’s.

  • Spark January 27, 2011, 9:09 pm

    How do you Skype all the time if he’s in jail?

    Reply Link
    • Anne (I Go To 11) January 28, 2011, 9:49 am

      I was wondering that, too.

      Reply Link
    • thyme February 1, 2011, 1:17 pm

      I think maybe they used to skype all the time, and he was just recently incarcerated? It sounds like it might not be a very long stint in jail?

      Reply Link
  • Avatar photo

    bitter gay mark January 28, 2011, 3:33 am

    Baby, you’ve hitched your wagon to a real star here… You think that he will one day “provide for you?” Good luck with that. Maybe you should, I dunno, grow the heck up and provide for yourself. The nicer part of me is sorely tempted to give a well thought out and constructive lecture of how inane and foolhardy and dangerous this relationship of yours truly is… But you know what? My patience with fools who go out of their way to wreck their own lives is simply at an end. If this is the life you want! Have at it. Frankly, it is perhaps about as good as anyone with your intellect can expect…

    Reply Link
    • baby.blanka January 28, 2011, 10:12 am

      I liked your response up until the end – while I don’t see any need to insult the LW – I do feel that she is basing her hopes and dreams on no real evidence and that’s scary. She did write to Wendy because she is confused… hopefully Wendy’s response and a little bit of looking at her situation from the outside will help clear things up for her.

      Reply Link
  • blackbird January 28, 2011, 5:25 am

    ASIDE from the alcoholism, the 6-hour distance, the whole being-in-jail thing, and all the other serious red flags mentioned above, sometimes the age difference is a problem in itself. I’m not knocking all couples who have major age differences between them; I know a few couples who are happily married and have children who are 10+ years apart. But sometimes, it says a lot about one (or both) of the people who are in the relationship.
    When I was 19, I dated a 30-year-old. Once the excitement and scandal wore off about a year after it started, I realized what he really was: kind of pathetic. He was terrible at meeting people his own age, and could only really relate to kids my age because he was so immature. I’ve dated plenty, and he was by far the biggest child ever when it came to arguments, and was incredibly sensitive. He would regularly unfriend me on Facebook after particularly bad fights. He ALWAYS hit below the belt in disagreements, and really didn’t know how to be in an adult relationship (also, he wouldn’t even buy me alcohol when I was underage. What gives?!). On top of all this, he kept me from what I should be doing as a college kid: going out and having fun. He never wanted to meet my friends or go anywhere; we always ended up watching TV and going to bed by 11.
    I stayed with him for two years, and I seriously regret all the people I could have met and boys I could have dated. While settling down may sound attractive right now, it won’t in a few years when you’ve realized everything that you’ve missed out on.
    I know it’s hard advice to hear and I’m sure you’ve heard it before, but live your life! You don’t want to spend your first years as an independent adult tied down to someone who’s six hours away and incarcerated. I don’t see what you see in this guy at all. And if he’s worth it, he’ll be waiting for you at the end of his battle as a fully-functioning (and ready) boyfriend.

    Reply Link
  • ArtsyGirly January 28, 2011, 5:55 am

    Oh hug** to BGM.
    Wow sweetie it is time for a wake up call. You have looked out at the wide world and found this guy as your ideal partner. Not only is he older than you (not always a bad thing but here it is) who is serving time in prison because of his alcoholism. You are WAY to young to be settling for this type of guy. In fact my 90 year old grandmother is too young to settle for him. Now make sure you are not looking at this guy as someone you can ‘save’ or ‘fix’ because you CANNOT EVER save someone else.

    Now some of your language suggests to me that you really want to enter into a mature relationship and settle down quickly. You said you want someone to ‘take’ care of you. Does this mean that you really aren’t interested in working and instead would like to be a housewife and mother (no judgment from me, since my mother did this)? If this is the case you are really in the wrong relationship. This man at 30 cannot take care of himself, let alone take care of you. If he was convicted of a felony than he is going to be barred from a lot of high paying occupations. If you want to settle down early, go meet some nice guy in the law library or medical buildings on your campus.

    Also keep in mind that alcoholism runs in families. If you want to have children with this guy you have to be proactive. I am not saying that alcoholics should never be allowed to have children, but that those who are active recovery make sure they are more diligent than someone who does not suffer from this disease would be .

    Please LW step back and say to yourself, ‘if my friend was in this situation what would I tell her?’

    Reply Link
  • Avatar photo

    Skyblossom January 28, 2011, 7:19 am

    Many communities now have their court records online. You can find them with a Google search if you type – City public access court records. Put the name of your city where I put city. You can also search county records by listing the county and state and then public access court records. If you boyfriend was arrested by police he will probably have city court records and if he was arrested by a sherrifs department he will have county court records. Please do a search under his name for every place that you know he has lived. Find out what kind of life he has been leading. It can’t be good or he wouldn’t be in jail. If he has a common name you will also need to know his date of birth and middle name or initial.

    Reply Link
    • Avatar photo

      Skyblossom January 28, 2011, 7:50 am

      If you do the Google search the links at the top of the page will probably be private, for profit sites. Don’t use these. Continue down the page until you find the free public records for your community. My city comes up about the middle of the page.

      Reply Link
  • Avatar photo

    fast eddie January 28, 2011, 8:35 am

    This guy’s not in jail because inmates don’t have access to the internet. He’s a predator and using the internet to lure naive women with a sob story. Call the police and report it NOW! This girl’s in danger.

    Reply Link
    • Tudor Princess January 28, 2011, 4:38 pm

      Many inmates who are considered low risk have access to computers. Many of them get to work answering phones and doing customer service work. It is highly possible that this guy in one of them.

      Though, I do think reporting it is a good idea. I doubt this guy is being honest with this girl at all.

      Reply Link
  • Avatar photo

    bitter gay mark January 28, 2011, 11:54 am

    The other possibility that crosses my mind is that this is a fake letter. Maybe it’s bogus? I dunno…is anybody really this clueless? Even at 18? Maybe somebody is just duping Wendy…

    Reply Link
  • spaceboy761 January 28, 2011, 3:53 pm

    I would opt for a 30-year old alcoholic pedo that was locked up about one or two hours away, tops. Distance can be a real relationship killer!

    Reply Link

Leave a Comment