Dear Life Kit: I'm not sure about her sexuality. Should I try to kiss her anyway?

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Dear Life Kit is NPR's advice column, where experts answer tricky questions about relationships, social etiquette, work culture and more. 

Send us your anonymous questions. For our next episode, we're looking for your queries on doubt and decision-making in relationships. 

These questions were answered by Haley Nahman of the Maybe Baby newsletter and podcast, and Danny Nelson, co-host of Maybe Baby's Dear Danny advice series. The conversation has been edited for length and clarity.

Dear Life Kit, I'm a 60-year-old widower and recently met a 52-year-old widow. 

We get along great. She's smart as hell and as sarcastic as I am. We've told each other we like each other and have expressed affection in nonphysical ways. 

The issue is that she's widowed from her wife. I'm also widowed from my wife, who was with women before she met me. I'm very open about people's sexuality, and we've briefly discussed sexuality, but I have no idea how fluid she may be, if at all. 

I would like nothing better than to kiss her. I felt at least a couple moments would have been perfect for that, yet I hesitated. I don't want to chase her away. Any advice on how to proceed? —More Than Friends

Nahman: This one is so sweet. We've lost a lot of romance in the younger generations.

My first impression is I don't think a kiss is where to start here. I think he could say, "I enjoy being friends with you, but would you ever be down to go on a date with me, or is that not your thing?" It could be as simple as that and easy as that.

A photo collage shows a Polaroid photo with the image of a child's teddy bear lying in an empty wooden chair in front of a green wall. In the foreground, a photo of a man's lower body, wearing dress clothes and a backpack with his hands in his pocket, walks out of the frame.

Nelson: Definitely. If he wants to pursue this and he actually treasures the friendship so much so that he doesn't want to lose it, the first course of action is to come to terms in his own heart about being completely OK remaining where they are now. Then it will be safe for him to move ahead.

Nahman: There's always a risk with putting yourself out there, but there's a risk with not. But I think they're at an age and experience level where they could weather something like this.

Dear Life Kit, My partner of six years and I are considering taking the next step together: getting married and having kids. 

While starting a family is something we both want in life, I am reluctant to commit to him because I can't stand his family. They're extremely rude to me and constantly belittle me, my background and my culture. 

I just can’t imagine raising my kids in a mixed cultural household where their closest extended family doesn't understand and celebrate their unique heritage. I've told him how I feel about the situation, and we both feel stuck. We feel that confronting his family would be awkward and drive a wedge between my partner and them, which is the last thing I want. I feel like the only options are to suck it up or move on. —No Thanks Fam

Nahman: I think this is the partner's responsibility. He needs to stand up for her and tell his parents they're not going to have a relationship with their grandchildren if they don't respect her.

He needs to show her that she's safe and that he absolutely hears her on everything she's saying and agrees. Hopefully he sees it the same way. If she feels belittled by him in any way, that's a different conversation.

She also needs to be incredibly clear with her partner about her fears and doubts and what she needs him to do.

A collage that shows an adult woman nuzzling her face into a small fluffy dog. The dog is looking over her shoulder. The woman is rendered in transparent tones and illustrated hearts hover over her and the dog's faces. Another woman, seen from behind, looks on to the scene from the side as white squiggles emanate from her, symbolizing jealousy.

Nelson: It's curious to me to be with somebody for six years and be talking about starting a family and then be like, actually, his in-laws are so awful that maybe I should just break up and start all over. It feels like a really extreme response for such a long relationship. It's worthwhile to consider if actually you're just having doubts in the relationship proper.

The podcast episode was produced by Andee Tagle. The digital story was edited by Meghan Keane. The visual editor is Beck Harlan. We'd love to hear from you. Leave us a voicemail at 202-216-9823, or email us at [email protected].

Listen to Life Kit on Apple Podcasts and Spotify, and sign up for our newsletter. Follow us on Instagram: @nprlifekit.

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