How to Do It

My Boyfriend Thinks It’s Fine His 34-Year-Old Friend Is Flirting With a Teenage Girl

Did I mention he’s nine years younger than me?

Older man flirting with teenager in front of a neon sign flashing NO 18.
Photo illustration by Slate. Photos by MRBIG_PHOTOGRAPHY/iStock/Getty Images Plus and Marie_Liss/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to Nothing’s too small (or big).

Dear How to Do It,

I’m a straight woman in my mid-30s, and I’m dating “John,” who is about nine years younger than I am. He was brought up religious and married his first girlfriend, and well, shocker, that didn’t work out. It was a horrible time for him, and John still carries a lot of baggage from that. He has a good friend from that period of his life, “Anders,” who understands a lot of his hurt and is valuable to him because of that.

I personally hate Anders. One of the first things John told me about Anders was that he was having a “slut year,” in which he was sleeping with as many women as possible post-divorce. I don’t care about that, but John mentioned that Anders was almost exclusively sleeping with women from around 19 to 22 or 23 years of age. Anders is 34, so that’s 10 to 15 years younger. I was creeped out and told John so, and basically got a “look who’s talking” response since I’m dating him. I argued that we’re closer in age and that he’s older than these women and therefore more mature, and that the two dynamics—older man/younger woman and older woman/younger man—aren’t comparable. We ended the conversation pleasantly enough, but a few weeks later, Anders called while we were watching TV and my hackles went up. John seemed tense talking to him after a few moments, and said “Anders, are you allowed to take her over state lines?” then laughed nervously. I ended up on the phone with John and someone in the car with Anders on a road trip, who turned out to be a 17-year-old girl who was a friend of Anders’ daughter’s babysitter. As soon as her age was mentioned, I loudly said I wanted no part of the conversation.

When John got off the phone later, I confronted him. He said that yes, it was weird, but then made a number of excuses for Anders being around with this girl. (Anders is “sex positive”; we don’t know why they were together; Anders “is an actor.”) I asked if Anders was sleeping with her, and he said no, but could only vouch as proof that he “knew Anders wouldn’t.” When I asked if he thought Anders was waiting for this girl to turn 18, he couldn’t say no. The evening ended with me staring at John and saying “She was born in 2002” several times while he got increasingly flustered. After going to bed, I had fleeting thoughts of calling the cops, but as they were across the country and I had little information, that seemed to be a dead end. But I honestly haven’t ruled it out if I find out they’re sleeping together. I really want my boyfriend to realize what a scuzz his friend is being and confront him, even in a low-key way, especially as concerns the 17-year-old. Am I being nuts? Should I let this go?

—May December

Dear MD,

I see why this raised your hackles. But keep in mind age of consent laws vary wildly state by state, and the police generally frown upon frivolous calls. Sixteen is pretty typical in the U.S., although certain states (like California) and smaller territorial divisions have higher ages of consent, or laws about how much older the older partner can legally be. So your first action should be to find out which states are involved and look into the local laws. Even if this could be illegal, try to think of the potential effect on the girl of officers bursting in. It’s hard to measure your likelihood to help or harm the actual situation if you get involved.

Now, for what you can control. Are you sure you want to be dating the kind of guy who defends relationships that you find inappropriate? This strikes me as a mismatch of ethics, which can be a clear red flag. I know you want John to realize how generally gross Anders’ sexual fixation on youth is to you, but I’m wondering if there are some things that you need to realize about John. It can be tempting to think people will grow out of friendships with controversial people, but that isn’t necessarily the case.

Your relationship with John is different than what Anders is doing for many reasons. But human brains are still developing significantly until around age 25, and John is just on the other side of that ledge. As much as it can be tempting to meddle in the emotional development of younger partners, you aren’t their parent and you never will be. You can state your opinion, you can have a discussion, or even an argument, but you can’t tell him what to do, or force him to give up on his, yes, scuzzy friend.

Dear How to Do It,

I’m a woman in my late 20s dating from apps after a relationship. I’m currently seeing two men that I met at roughly the same time and hit it off with. We’ve had no formal talks about being exclusive on either side. I have an IUD, and after our first couple times, I’ve fallen into a habit of not using condoms with either guy. My question is what level of obligation I have to bring up to these guys that they’re not the only person I’m banging without protection? I think it’s assumed—I assume they’re seeing other people, too—but I do wonder if they might not be aware of what I’m doing. What am I required to disclose, if anything?


Dear Unwrapped,

My unilateral decision: You are obligated to tell your partners that you’re also skipping condoms with other people.

I also find it alarming that you describe not using condoms as something you fell into as opposed to something you chose. You see, ideally, you’d have a talk about being fluid-bonded before throwing condoms out the window. Ideally, everyone involved would get a fresh STI screening and know their status. And, ideally, you’d have access to the best condom fit and material for you and that specific partner. All forms of safer sex have a failure rate, and using more than one method is best practices.

You don’t mention STI testing, so while you’re here, I’d like to mention that syphilis, gonorrhea, and chlamydia rates are on the rise, and HIV is still a risk. Have you tried polyisoprene condoms? Or Lelo’s latex Hex condoms? (Disclosure: I’ve done promotional work for Lelo.) Are the guys wearing the right size? I’m invested in finding you a condom that works for you, so write to me if I can help more.

Dear How to Do It,

I’m a 46-year-old straight woman and I love sex. I just got out of a seven-year relationship, the last year of which there was no sex, and I’m being pretty adventurous. I’ve slept with four guys in the last two months, ranging in age from 29 to 50, and here’s the problem: While the sex has ranged from bleh to great, I’m not getting good clitoral stimulation, and I haven’t had a clitoral orgasm. And I love orgasms. (Who doesn’t?!)

When I masturbate this is not a problem, so I know it’s not a physical issue. At one point, I had to ask myself if men had forgotten how to touch and lick the clit! I’ve communicated my needs verbally, provided instructions, helped out … I don’t know what to do. I do wonder if some of it is hormonal (I’m perimenopausal), if I’m just more sensitive. It seems like they start in too rough, even though I do communicate, but then I get to a point where I know it’s not going to happen, so I focus on other things. This last weekend, I had sex with the 29-year-old (three times in a day, and each session an hour plus!), and it was amazing, great g-spot stimulation and all, but still: no clitoral orgasm.

I don’t have to have one every time, but I’m wondering if what used to work for me doesn’t anymore because of physical or hormonal changes. My plan for the next time I have sex is to make sure it’s slow and to have him focus on giving me an orgasm with fingers or tongue, but I’d appreciate any thoughts or advice you have.


Dear Spotty,

Sensitivity is beautiful! Guys can be a bit thick when it comes to gentle touch. Anecdotally, guys who’ve been circumcised seem to have an even more difficult time learning how to give gentle touch than guys who are uncut. My advice to you is to be incredibly blunt, and reiterate yourself a few times during the pre-sex conversation. Like, “I like to be touched incredibly gently. Tease me. Make the lightest licks you can possibly make. Hover your tongue over my clitoris and breathe on it. Touch me super gently. Like impossibly so.”

Guys also tend to slip back to firm touch. Correct them mid-sex. Say, “Hey, that gentle touch you were doing earlier was great. Can we go back to that?” Say it over and over if you have to. Who am I kidding—say it over and over because you almost certainly will have to. Another way you can underline how you like to be touched is by masturbating in front of your partner, or even guiding his fingers with your own.

As to perimenopausal factors, bring it up with your medical professional the next time you see them, but I somewhat doubt that’s a factor here since you say you have clitoral orgasms when you’re masturbating. You also might consider joining a Facebook group or other forum for women in that stage of their lives. You can gain a lot of insight from other people’s woes and help others by sharing your own.


More How to Do It

Recently, I went on a date with a woman I met on a dating app. As we were leaving, I leaned to kiss her. She pulled away and was visibly distressed. I apologized and said I misread the situation, and she quickly made an excuse to leave. It was embarrassing and a little deflating, but it happens. I didn’t hear from her for a few days, when she suddenly texted me a long and detailed message saying, among other things, that I had “nearly assaulted” her and it was never OK to go in for a kiss without asking first. She said I should look hard at my understanding of consent. I was tempted to tell her she was being over the top, but she was upset so I rode it out. Am I right to think she was being over the top? It’s fine if she wants men to ask her before they kiss her, but I do not think that is standard practice. Is it?