Dear Wendy
Dear Wendy

Shortcuts: “What’s With all The Picture Requests on Craigslist Casual Ads?”

It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to go.

I am a gay man and I go onto Craigslist looking for casual M4M sex. What disturbs me is how many people want a pic first. What is wrong with these people? Married men have sent me pics before. Don’t they realize what goes up in the cloud stays there? And the younger people show both face and body completely. Why don’t they understand that, down the road when jobs come up that they are applying for, prospective employers might tell them, “We came across this info and these pics when you were younger.” They might be older then and with families. Would they still be that open if they realized this? People have no modesty. I mean, I like having sex but behind closed doors where only they see and god knows that’s it. — M4M, No Pic Required

As the young people say: you do you. Worry about yourself, your own potential job opportunities and future families, and the effect your current behavior may have on those things. But if you’re finding that your own discretion is keeping you from the casual sex you desire or is limiting your potential partners too much to be enjoyable, you need to either find a different game or try an alternate way of playing.

My boyfriend and I are 50 years old and in a great place in our lives. For the past year, we have not used condoms. He had some in his shaving bag (we both travel for work) and a few months back he stopped bring his shaving bag. I assumed no more condoms, but this morning, while looking for car keys, there they were — moved to a bag he carries with him everywhere he goes. My heart broke! He said he just never threw them out and hasn’t even thought about them. If that is the case, then why did he transfer them when repacking and still have them? He’s a good man and we’re together 24/7 most of the time. BUT should I be concerned and should I leave? I can’t go through this again with a man. — No Need for Condoms

Hmm, it sound like your boyfriend isn’t the only person in this relationship who needs to unpack some of his baggage. It’s entirely possible and reasonable to think the condoms have always been in your boyfriend’s bag — and not just moved from a different bag, but always in THIS bag — and that he truly hasn’t given them a thought and never got around to throwing them out. That you “don’t want to go through this again with a man” says much more about you and where your head is than where he is. Especially if where he is is actually with YOU 24/7, like you say. Let this go, unpack some of your emotional baggage, and accept that “this man” isn’t the same man who has hurt you in the past.

My boyfriend and I are cousins, but not blood cousins. He was adopted. It’s been 10 months. At first he was so sweet, which is probably why I started falling for him. His father (my uncle) told me that his son confessed to him one day that he thinks he’s falling in love. After that, I stupidly got pregnant by him the first time we had sex. Since then, he’s changed so much! He acts like such a jerk at times. One day he texted me, “I don’t want you falling in love with me or anything, so I don’t give things.” I was joking around and had texted earlier: You’d better make it up to me next time with a flower or something.” Seriously, who does he think he is? Should I try to give him up? Should I confront him and tell him how I feel or just never answer his text? I am so freaking emotional, and he has turned cold as ice. What should I do, Wendy? — Kissing Cousins and More

Oh, dear. If you’re pregnant (by your cousin, no less), you have bigger things to worry about than getting your boyfriend to give you a flower. Neither of you sounds mature enough or ready for parenthood, and your relationship is certainly not ready for co-parenthood, so I would urge you to shift your focus from relationship game-playing to figuring out what to do about the baby on the way. If you want to continue your pregnancy, please, please, please consider adoption.


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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.

27 comments… add one
  • Laura Hope December 12, 2014, 8:27 am

    LW1–I agree with you. If you think about it, your children, grandchildren, great grandchildren etc. etc. will all have access to these photos. Not how I’d want to be remembered.

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    • Addie Pray December 12, 2014, 10:18 am

      Agreed but this LW seems to be spending way too much time and energy worrying about other people.

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      • RedroverRedrover December 12, 2014, 11:10 am

        I think it boils down to that he doesn’t want to give his pic out, which makes it hard for him to get that sweet sweet lovin’.

  • Miss MJ December 12, 2014, 8:28 am

    Oh, my god, I can’t even imagine being a kid and having to explain to people that my parents aren’t blood cousins even though my grandparents are siblings. Anyway, even without the cousin thing, LW3, your situation sounds like a mess. Dump your cousin/boyfriend and make a decision about your baby. Wendy’s suggestions are good ones. And maybe you should contact LW2 about getting some of those unneeded condoms that her BF never got around to throwing away.

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  • mrmidtwenties December 12, 2014, 8:59 am

    Wait a second, people use craigslist still to hook up? I thought that’s why Tinder, Grinder, and the like existed…

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    • Addie Pray December 12, 2014, 10:14 am

      It’s for hookups among people without smart phones?

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  • gigi December 12, 2014, 9:18 am

    Well for heaven’s sake LW1, so you would seriously hook up with a casual encounter sight unseen? Egads! I would never hook up with anyone I hadn’t seen a picture of, seriously! All the more reason to read CL for entertainment only! You can’t trust strangers not to spread your pics around. Like Mr.Mid said, use the websites people. There are still creepers on there, but not as many & if its a paid website, they have more incentive to behave discretely. There is also such a thing as pictures with your face edited out.

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  • Fabelle December 12, 2014, 9:52 am

    My parents are “cousins” via adoption also, so youse all better check yo’selves when commenting for LW3

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    • FireStar December 12, 2014, 11:16 am

      Do you mind me asking – were your grandparents happy – or upset? Because family holiday plans would be so much easier if you are all from the same family…

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      • Fabelle December 12, 2014, 11:36 am

        Haha my grandparents were not happy, but mostly because they thought it was a bad match…? Still everyone remained close (& I actually only recently started thinking of it as one family, brought on by when I was talking to my bf saying this and that about my mom and dad’s “side” of the family, he goes “but you don’t have sides, there’s only one side?? Your mom’s father is your dad’s uncle.” And my brain was like mindfuuuuck. I guess I hardly ever consider the actually relations??

    • RedroverRedrover December 12, 2014, 11:18 am

      LW3, I found condoms in a bag I use often, just a couple weeks ago. It was the bag I used to use to bring over to my now-husband’s while we were still dating. They’re just there, I don’t even think of them. They were in a pocket of the bag I don’t really use. It doesn’t mean I’m planning on cheating on my husband. Do you never just leave things sitting somewhere and forget about them? One time I found a hundred bucks in a coat!

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      • RedroverRedrover December 12, 2014, 11:19 am

        What, how did this reply get here? Sorry Fabelle, this was supposed to be standalone.

      • MissDre December 12, 2014, 11:27 am

        Me too, I have a drawer full of condoms. I just never bothered to throw them out.

      • SpaceySteph December 12, 2014, 11:54 am

        Ick. If you come across condoms you forgot were there, you need to throw them out immediately. Condoms expire, folks. Buy fresh for every new affair! 😉

      • Miel December 12, 2014, 12:02 pm

        Thank you ! My boyfriend still has a bag of all the free condoms he got in college and always kept “in case he would need them”. I was like “throw them away!”. He didn’t even know they had an expiration date, and they were all like 5 years expired. Ugh !

      • SpaceySteph December 12, 2014, 12:17 pm

        This totally reminds me of a Friends episode: They should put that on the box!

      • SpaceySteph December 12, 2014, 12:20 pm

        In seriousness though, my ex boyfriend and I had an old condom break on us one. Ripped wide open down the side. We didn’t usually use condoms– I was on BC but then was taking antibiotics so we found a condom in the drawer and used it.

        Now I religiously throw out condoms even a day after their expiration date. Not a chance worth taking.

      • RedroverRedrover December 12, 2014, 2:25 pm

        Oh, I’m not gonna use them! I’m married and we’re done with condoms. If I get pregnant again we’ll have the baby. When we decide we’re done with babies it’s snip snip. Birth control time is done! 🙂

    • MissDre December 12, 2014, 11:28 am

      LoL my dad had a relationship with his aunt. Not his blood aunt — she’s his blood uncle’s wife (mother’s brother’s wife lol — the uncle passed away though). It was really weird when Aunt Betty came to visit and she was sleeping in my dad’s bed.

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  • Portia December 12, 2014, 10:51 am

    I totally agree with LW1, sending pics like that out into the interwebs is a risky proposition. Then again, the LW is looking for hookups on CL, which is itself risky. Everyone has their own level of risk that they’re willing to take on (which includes agreeing to hookup sight-unseen, like the LW).

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  • joanna December 12, 2014, 11:02 am

    This is why I don’t ask for naked pics from hook-ups nor give them. Show me your face picture. Chances are if I like that, I’ll like the rest of you.

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    • joanna December 12, 2014, 11:24 am

      In the world of hook-ups though, isn’t craigslist like the bottom of the barrel?

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  • mylaray December 12, 2014, 11:03 am

    Gosh LW1, you’re so judgy. You’re on Craigslist trolling for sex with strangers and judging others that they send pictures of themselves. There is so much on the Internet and the chance of a person you know in real life finding something like that is slim. It’s going to matter less and less. Take your faux concern somewhere else. If you don’t like the quality of hookups on Craigslist, then find another place.

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  • SpaceySteph December 12, 2014, 11:56 am

    LW1- Snapchat.
    LW2- Therapy.
    LW3- abortion clinic or adoption agency, then therapy, and as soon as you’re done being pregnant… birth control. (LW 2 may have some condoms you can take off her hands.)

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  • Lyra December 12, 2014, 12:09 pm

    LW2…if you’re so worked up and worried about this very minor thing I think you need to think about if you trust your boyfriend. I mean think about it, you’re asking if you should leave over this. And you say you’re with him 24/7 (which isn’t the healthiest either). I get being burned once and not wanting it to happen again, but if you’re so worked up that you write in to a relationship advice columnist over this trivial thing, it’s definitely worth some introspection.

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    • mylaray December 12, 2014, 12:41 pm

      Yup, I agree. Also, why is she looking through his stuff all the time? If you go looking for a sign he is cheating, you will find something that puts those pieces together, when it’s not logical at all.

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  • kaluu December 12, 2014, 2:05 pm

    1. Snap chat is a good suggestion. (Although they were hacked recently) Maybe face time too? Do they need a naked pic? What’s wrong with a tasteful shot of your torso-head in a form fitting shirt emailed to someone ? How would that ruin your life? Maybe you should not tell your hookups your real name so that future employers couldn’t find the pic anyways. Can you perhaps make a new email without your name… 3. If you’re having this baby relax, don’t expect anything, don’t be rude and immature to your bf/cousin, sit back and analyse how he acts to you, and make a decision about the baby /your relationship from observing him and asking important questions. He seems kind of rude so ask the questions at a good time in a nice way to minimize fighting. Even if you’re not going to be a couple, there’s no need to be mean to each other. Take it slow.

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