Dear Wendy
Dear Wendy

Shortcuts: “My Boyfriend Follows Naked Women on Instagram”

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.

My boyfriend is 35 and I’m 21. He likes asses. I don’t have a big one so I get insecure because he loves them! He follows naked girls on IG all the time, and , when I’ve said something to him about it, he just says it’s for entertainment. He follows like 2-3 new ones every week. I repeatedly tell him how it makes me feel, but he continuously tells me it’s just for entertainment. I don’t know what I’m supposed to do or how to even approach it anymore. Is it something I should worry about? We’re sexually active with each other, we live together, and he doesn’t have a lock on his phone. He doesn’t “like” the pictures, but I still feel like I’m not good enough. — No Big Ass

That your boyfriend is 35 and you’re only 21 is already suspicious. That he continues to follow 2-3 naked women on IG each week despite your expressed insecurity, telling you it’s “just for entertainment,” is another clue the guy is sleazy. Do yourself a favor and dodge this bullet before you get hit. In other words: MOA.

My boyfriend and I have been separated for four months. I have been staying over two to three times a week. Last Friday, I walked in on him in bed with my ex best friend. They were both drunk. He says nothing happened and they had just gotten home from a nightclub. He says he would never touch her because she is an ex-prostitute and he has higher standards. The point is he’s fighting to get me back but still won’t answer my questions about her. I’m so confused. Please help. I still love him. — Not Over Him

It doesn’t sound like he’s fighting that hard, OR that you are putting up much resistance if you’re staying at his place two to three times a week. You caught him in bed with another woman. How can it be spelled out any more clearly for you? You aren’t the only person he’s sleeping with. Get yourself tested and MOA. Four months is a long enough time to pretend to be broken up. Just break up for real and start the healing process. If you actually stay away, you’ll probably be over him by Christmas.

My boyfriend is a nice, sweet guy who loves buying me gifts. Recently he promised to make my friend’s birthday the best, so he gave her money to buy whatever she wants as a gift and has offered to buy her pizzas for dinner. But then he lied to me and said my friend asked for the pizza. I feel insecure. I’m proud of him, but it’s too much that he’s lying about the pizza. What to do? — Insecure Over Pizza

Your boyfriend gave your friend money to buy herself a gift from him and it’s the pizza dinner that’s pushing you over the edge? Really? Either way, just tell him you’re not comfortable with him buying your friend gifts (including pizza) and that, in the future, you’d prefer the two of you give gifts to your friends together, from both of you, or that he not give your friends gifts at all without clearing it with you first. And that goes double for pizza dinners.


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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.

26 comments… add one
  • Raccoon eyes October 31, 2014, 8:55 am

    LW1: If a man is 35 years old and doesnt know how to be a grown up and be in a relationship (by not making his GF feel insecure and blatantly looking at naked women in an inyourface kinda way), then his ship has sailed. (As an aside: I dont do Instagram, nor understand it [or care to], but my understanding is that profiles or whatever are viewable to others…so it is obvious to her what he is doing and hence an “inyourface kinda way.”)
    LW2: If you are still sleeping over that much, you arent broken up- that is just words, presumably because you want him to change or treat you better or somesuch. His actions are that you are broken up. Time for you to act like it too by getting some distance. Like, really far away.
    LW3: Huh? Why is he promising to make your “friend’s birthday the best”? Kinda weird. Couldnt she have bought said pizza with her cash money?

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  • FireStar October 31, 2014, 9:04 am

    Is buying pizza code for something? I can’t keep up with the younger generation….

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    • something random October 31, 2014, 9:13 am

      Yeah, I didn’t even understand the question until I read Wendy’s response. It still doesn’t make sense to me, but Wendy’s answer still applies.

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    • RedroverRedrover October 31, 2014, 10:00 am

      Is IG what they call instagram now? Sigh. No idea, with any of this stuff.

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    • MissDre October 31, 2014, 10:04 am

      LoL I work for a dance studio, overflowing with teenage girls, and I manage a lot of the social media marketing. The things I see these kids posting on Instagram…. LoL. Yesterday it was “The first 3 boys that like this post will get their name written on my wrist in permanent marker! Only brave girls will repost!” I just can’t help but laugh because I probably would have done that in 6th grade…

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    • fast eddie November 1, 2014, 8:16 pm

      Naked women are on IG? Don’t wait up I’ll be a while getting back….

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  • tangerbean October 31, 2014, 9:08 am

    This is the weirdest bunch of questions…

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    • Amanda October 31, 2014, 9:44 am

      I thought the same thing. I gave up on trying to follow 2 & 3.

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  • eelliinnss October 31, 2014, 9:16 am


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  • something random October 31, 2014, 9:50 am

    That’s interesting. I agree that most 21 year olds are still on the heel of the teen years and are like little newborn adults. But I think alot seem to come into their own shortly thereafter especially once they get out of college. I think of a 24 year old a grown up. Less experienced? Sure. But still a grown-up. I wonder if people who do longer stints of education (grad, law, medical) school feel incubated a little longer? It seems urban areas really cling on to the the young, fun, party lifestyle? I watch shows like Newgirl and thirty year olds are still running around like they are in college. It seems elective to me.

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    • shakeourtree October 31, 2014, 12:12 pm

      I worked full time for three years between undergrad and law school, and sometimes I feel like an old woman compared to my peers who came straight from undergrad. It really is like undergrad 2.0 for some of them.

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  • Taylor October 31, 2014, 10:05 am

    These are less scary than last weeks – no kidlets involved.
    Happy Halloween!

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    • Wendy_not_Wendy October 31, 2014, 10:26 am

      Except for the kids in letter #3, of course 😉

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      • Taylor October 31, 2014, 10:50 am

        Hah! I see what you did there!

  • Dear Wendy October 31, 2014, 9:29 am

    From 2_j (who accidentally commented in the previous post):
    Honestly, I really do not think being 35 and having a younger gf, 21, is suspicious at all.. just my opinion. I think that’s a bit harsh to say. They are both grown adults, age is just a number…no? Knowing your gf follows you or can see what you post or like on instagram yet still continues to do stuff on there that makes you uncomfortable and basically not caring is quite shitty though.

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    • othy October 31, 2014, 10:29 am

      A 35 yo dating a 21 yo is suspicious, but not damning. I’ve known some really mature 21 year olds my life (and many really immature 35 year olds). But, now that I’m in my 30s, 21 just seems really really young. And this coupled by a disrespectful boyfriend (who isn’t very good at being discrete about naked woman viewing after his girlfriend said it made her uncomfortable) makes it time to MOA.

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    • Dear Wendy October 31, 2014, 9:29 am

      I would argue that most 21-year-olds are, in fact, really “grown adults.” Legally, sure. But emotionally, psychologically? Not most of them. Many haven’t even left home or experienced any financial independence yet. There’s just such an enormous gulf between early 20s and, say, 28+. When I was 21, I dated a guy who was 28 (so , half the age difference as the LW and her boyfriend) and even that seemed like a pretty big difference. The flip side is that that is the same age difference between Drew and me and it’s a complete non-issue and has been since we met (I was 29 when we met and he was 36). There are exceptions, of course, but I’d say most people (in America, anyway) are still more like adolescents at 21 than they are like adults.

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      • 2_j October 31, 2014, 9:53 am

        i so put this in the wrong section haha. Yes i agree Wendy. I think it depends on the people for sure. I was 22 (years ago) and my gf at the time was 36. We had a long term healthy relationship, caught a lot of flack for it but we didn’t care and were mature consenting adults.

      • RedroverRedrover October 31, 2014, 9:59 am

        I think it *can* be fine, as you say it was for you, but it’s often not. Sometimes people meet and click and hey, one of them is way older than the other. That’s not a big deal. But more often the older one is either unable to get a partner their own age (usually because of issues they have), or they don’t want a partner their own age (again, because of issues they have). That’s when it’s a problem.

        I’ve dated a guy older than me, and yeah, he was a highschool dropout who worked nights at a fastfood restaurant. Not a match for me. But when I was in highschool, he seemed awesome because he didn’t have to go to school, he had money, he was older (always exciting), he could drink, etc. He wasn’t a sleaze or anything, but he wasn’t exactly a catch for women his own age, so he dated young. Other guys date young because they’re a mess and younger girls don’t realize it. I know a guy like this, and I feel so bad for him, but he won’t even go after girls his own age because I think he’s scared that once they realize how screwed up he feels, they won’t want him. He’s not even really a mess, he just thinks he is. But that’s enough to make him hard to be with, I would imagine.

        And then some people are just sleazes and they purposely prey on younger ones who don’t know any better.

      • something random October 31, 2014, 10:07 am

        @RedRoverredrover I agree with this. I’ve seen it, too. I remember when I was 25 or 26 I had a friend who was 23 who ended up marrying someone who was 46. When she was dating him, I was the only one who told her it was a mistake. She ended up marrying him less than a year later. I don’t know what happened to her but the whole thing seemed to be based on her impulsive personality. I think she thought they were a match because her youth advantage somehow cancelled out her flaws.

        I also remember an older thirty something guy pursing me hard when I was 22. I almost considered going out with him (though I don’t think I would have). I ended up dating someone else. I remember having a hunch that there was something off about him not looking for women his own age. In hindsight and can see examples of glaring personality flaws that didn’t register at the time.

      • MissDre October 31, 2014, 9:56 am

        Oh my goodness, I’m 28 now and I’m not even close to the same person as when I was 21. At age 21 I *thought* I was so grown up and such an adult but in hindsight I kind of cringe when I think back to some of my immature behaviour and all the things I didn’t know…. I think my biggest “growing up” years, so far, have been between 25-28. I’m even amazed at my own personal growth since 25.
        Anyway, my point is that I agree with Wendy, that a 35 year old guy interested in 21 year old girls is creepy and speaks to his own emotional immaturity.

      • FireStar October 31, 2014, 10:31 am

        We have a friend who is 42 and he was asking if it was scandalous for him to date a 22 year old…we told him he couldn’t come by the house anymore if he did.

      • muchachaenlaventana October 31, 2014, 10:17 am

        Yeah my friend dated a 36 year old when she was 23 and she really liked him, he fell in love with her, and wanted to marry her but she was super young, having fun, dating lots of guys and ended up really breaking his heart. Obviously it *can* work, but early 20s and just graduated from college is miles away from a hopefully mature 30something (although this guy does not seem mature).

      • fast eddie November 1, 2014, 8:33 pm

        I agree with Wendy that a lot 21 YO (or older) people don’t act like I expect adults to act and a few young people are wise beyond their years. The entire spectrum of age difference exists in couples. I know two women that married men 10 years younger and they get along just great. Until the 1940s it was very common for very young women to marry older men. In some other modern cultures they still do. It’s only a matter of your own perspective.

  • RedroverRedrover October 31, 2014, 11:06 am

    What’s with all these letters where the LW says “he’s fighting so hard for us”. What does that even mean? Are they Romeo and Juliet and their families are trying to keep them apart?

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    • MissDre October 31, 2014, 11:12 am


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