How to Do It

My Daughter Approaches Her Relationships Far Too Seriously

How do I make her more carefree, like I was at her age?

Mother hugging daughter.
Photo illustration by Slate. Photo by Image Source/Getty Images.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

My 38-year-old daughter is a beautiful person, inside and out.  She is a talented artist, a college graduate with an art degree, a hard-working, fun loving, generous, and giving girl. Her problem is stubbornness, I guess, with a liberal dose of “choosing the wrong guy.” Her only two long-term relationships have been with two impossibly unsuitable dudes; but in each case, she’s refused to give up until the bitter end, 10 and six years, respectively. Currently she is mourning the end of the last one … trying desperately to rekindle things, even after moving out a year-and-a-half ago. She’s very lonely and suffers bouts of depression in which she drinks too much and gets fired from jobs, but won’t open herself to dating or meeting new people.

When I was in my 30s, before I finally married and settled down for good, I constantly met new guys to become infatuated and have adventures with. If one relationship ended, it was easy enough to strike up another one. So many fish in the sea … but my daughter doesn’t see things that way. How can I help my daughter to cultivate more of a devil-may-care attitude about men?

—Why So Serious?

Dear Why So Serious?

You are not your daughter, and your daughter isn’t you. She has a different approach to dating and relationships than you did, and that’s OK. I’m not sure you should try to cultivate a more frivolous air toward men in your daughter. She’s 38. She can make decisions for herself.

I do think she may need a therapist more than a new lover. Bouts of depression where one drinks to excess and loses employment sound concerning. As her parent, you should absolutely ask her to consider seeing a professional. Friends are conspicuously missing from your description of your daughter. Does she have close friends? If not, you should also encourage her to make some. Strong friendships are a crucial part of social engagement, and those, combined with therapy, may help set her up to make better romantic choices going forward.

Dear How to Do It,

I feel this need to have my husband dominate me. We’re both fairly young, in our early 20s. We got married a couple years back and everything has been great, except our sex life. He’s like my best friend, we get along extremely well, and he’s very sweet and loving, but I want something more intense. My last relationship was with a strong and quiet dominant type, who knew exactly how to make me submit.

My husband, on the other hand, is very vanilla. And last year, we had sex a grand total of 12 times in our first year of marriage. I’ve had multiple talks with him about how sex is very important to me, and I want to feel wanted. I’ve told him how I want to be dominated again and feel like I really need this. His answer is always how I make him feel like he’s not good enough, that all I want is sex, and it makes him feel like I’m cheating on him. Which obviously makes me feel guilty for even bringing up what I want and what I need. I’ve even brought up if we could open our marriage, and this was immediately shut down. I just want to feel controlled and put in my place sometimes. Is that so bad? My friends tell me to just leave him and be single for a while so I can find someone that satisfies me, but I love my husband very much and can’t stand the thought of losing him.

—Tell Me What to Do

Dear Tell Me What to Do,

You have a few options: stay and be unsatisfied, leave and take your chances finding someone suitable who meets your sexual desires, or force the issue of him being more sexual or y’all opening up.

I’m not the only advice columnist who wishes people would sort out their sexual compatibility before they get married for exactly this reason. You’re still young and you don’t mention children, so now’s as good a time as any to leave if that’s what you’re going to do.

Make a list of all your husband’s good qualities. Now make a list of all the sexual acts you desire that he isn’t interested in giving you. Weigh them. Imagine giving one list up forever. Imagine giving the other list up forever. Decide whether you’ll leave or stay depending on each possible response, from “Are there exact words you want to hear me demean you with?” through to “Absolutely never, I won’t speak of it again.” And then have the conversation one last time. Start by letting him know that the situation is dire for you. Be honest with him. Tell him that you love him, and can’t stand the thought of losing him, but that you have these sexual desires that are going deeply unmet. Ask him to work with you on solutions that might be functional for both of you. Give him space to come up with contributions. But if he doesn’t, the ultimate call about staying or going is up to you.

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Dear How to Do It,

I’m a straight lady and have had sex with a variety of men, but have only ever successfully done doggy-style once. Every other time, they’ve slipped out constantly or the angle hasn’t worked at all. Is there something wrong with me? If not, any tips to make things go smoother?

—Bad Dog

Dear Bad Dog,

Everybody’s body is different. You may not be shaped internally in a way that works well with doggy.

It’s still worth trying a few things—have you tried being still and letting your partner do all the movement? Have you tried having your partner be still while you do all the movement? You can go very slowly for a few thrusts to get an idea of what your range of motion is like, and it sounds like you may need to reduce that range. You might need to slow down your pace entirely.

Do you remember what worked about that one successful time? If so, there’s some useful information. Otherwise, experiment and practice.

Dear How to Do It,

I’m a straight woman who’s been seeing a man casually for several months (we met before quarantine). We are both in our 20s, and have a good connection personally and intellectually. At this point we’ve had sex around five or six times, and it’s been good if not mind-blowing. But it’s basically the same every time, in terms of the kind of foreplay we do, the positions, the order in which we do everything, etc. The predictability is kind of boring me.

I know the obvious answer here is to communicate, but what’s the best way to do so? Is it even necessary to discuss, or should I try to mix things up in the moment? There was one time when I initiated a different position than usual upon starting, which he was fine with, but also seemed mildly bemused by (like, “Oh, OK, we’re doing this? Sure.”). He had a similar reaction when I once brought a bullet vibrator to use during sex. There was a slight lack of enthusiasm in both these instances that made me feel awkward.

He seems happy with the way things are, and I don’t want to seem judgmental or unsatisfied or too demanding. Furthermore, I feel paradoxically shyer and more awkward with him than I have with previous sexual partners, even though I know him more and we have a deeper nonsexual connection (more casual = freer or looser, I suppose). I’m sure I’m overthinking this whole thing, and I would like to hear your thoughts!

Sir Mix-It-Up

Dear Sir Mix-It-Up,

You’re probably feeling shyer because you know him more and have a deeper nonsexual connection. The stakes are higher. There’s another question in this column that illustrates why you want to sort out your sexual compatibility sooner rather than later. The stakes are only going to keep increasing.

I’d pick a relaxed, private time and ask directly what your partner thought of the vibrator, and of the position variation you initiated. It doesn’t have to be fraught. “What’d you think of that vibrator?” will suffice. If he doesn’t know how to discuss it, or expresses discomfort with the vibrator, that’s a sign he might not be such a great match. But you won’t know until you try to talk about it.

Other conversation starters include “Where did you learn about sex?” and “Do you watch porn when you masturbate?” There’s also “You know what I’ve always wanted to try …” and “I’m really into kissing.” Or anal, or leather, or whatever your thing is.

What felt like a lack of enthusiasm on his part could’ve been surprise, shame, wariness, or any other of a number of reactions. Verbal discussion will give you a better idea of what was actually happening on his end, and you’ll have a better read on whether the two of you are a match sexually.

—Stoya

More How to Do It

I’m a bisexual woman in my early 30s, and I’ve been in a relationship with an amazing woman for the past nine months. We both care about each other deeply, and it’s the happiest and most stable relationship I’ve ever been in. Here’s the thing, though: Before her, I’d only ever slept with and dated men, while she’s dated almost exclusively women. I feel painfully inexperienced compared to her, which is uncomfortable for me because I’m used to being the more experienced one. It kind of feels like being a virgin all over again. For what it’s worth, these worries are all coming from me—she has never made me feel bad about my bisexuality or my past relationships with men. But I can’t stop worrying. To me, the sex in our relationship is great—but what if she thinks something is lacking? Mostly, I worry that I might not be as good as her exes (several of whom are “gold star” lesbians). How do I compete with that?