DEAR NATALIE: I started dating this guy recently and he likes to send me DMs on Instagram throughout the day with funny memes to look at. Well, the last two have not been funny. He found these videos of animals being brutalized and sent them to me. I thought (at first) that he was going to comment on how atrocious it was. But I was wrong. He thought it was funny. He was making fun of the situations and the animals. I’m a vegetarian and a huge animal lover so I was horrified by what he sent. I tried to talk about this with him but he told me I was being too sensitive and said “who cares about them, anyway.” I haven’t spoken to him in two days and he’s been blowing up my phone wondering why I won’t respond. I liked this guy a lot and now I’m questioning my judgment. Should I discuss with him again how I feel? Why does dating in your 30s have to be so terrible? Send help. -ANIMAL LOVER

DEAR ANIMAL LOVER: Cut ties with this guy immediately, take a long, hot shower and try to forget this ever happened. Whenever anyone laughs or mocks any creature in pain, that is a major red flag. This guy could have underlying anger issues and be a violent person. I know dating can be rough, but at least you figured this one out sooner than later. It’s a blessing in disguise that he showed his true colors so quickly. Dust yourself off and move on. There are plenty of fish in the sea -- and plenty who don’t find pleasure in another’s pain. 

DEAR NATALIE: My best friend just came out to me as trans. This wasn’t a huge surprise to me, and I am in total support of them. My girlfriend, however, is more conservative than I am. She thinks that my friend, who goes by Sharon now, is just going through a phase. I tried to explain to her that Sharon has been struggling with their identity for a long time and I was proud of them for their bravery. She just doesn’t seem to understand and is treating Sharon unkindly. It’s also turning me off that my girlfriend is acting like this, and so we are having issues. How do I resolve this situation? If this was our child -- and I wanted to have children with her -- would she still be reacting this way? I’m not sure what to do or say to help her understand. Any advice? -GIRLFRIEND IS TRANSPHOBIC

DEAR GIRLFRIEND IS TRANSPHOBIC: People can be afraid of what they don’t understand. Oftentimes, we mask our fear with outrage, anger and willful ignorance. We deflect and decide that we don’t want to know or understand because it’s uncomfortable. It’s not Sharon’s job to educate your girlfriend. It isn’t your job, either. Just because someone’s experience is different from our own doesn’t make it any less valuable, legitimate or real. I applaud you for standing by Sharon through this time in their life where they need support and the love of friends. Sharon has every right to live in a way that is most authentic to them, and I feel sorry that your girlfriend’s mind is so narrow that she won’t acknowledge what strength it took for them to embrace who they really are. I can understand why you are turned off, too. It’s hard when we pull back the curtain and see a side of someone that we didn’t realize was there. But the good news is that people can evolve. They can educate themselves, they can listen to those outside of their own experience, and they can create a space for tolerance in their own hearts. But it is a choice they have to make. And you have to make your choice, too. Is this the kind of person you want to build a life with? Maybe if you share your concerns with her, it will push her along her own journey. Or maybe it won’t. Either way, you have to decide what the future looks like for you and any potential children you bring into the world.

Please send your questions to Natalie Bencivenga to

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DEAR NATALIE: I have a close circle of friends. Well, I thought they were close. Recently, my one friend got engaged and some of my friends threw her an engagement party but I wasn't on the list. I found out about the party after they posted photos on Instagram. I confronted my one friend who coordinated the event and she said because of COVID, they only wanted to have about 15 people at her house. I couldn't help but roll my eyes because she wasn't concerned about the pandemic all year and was out way more than she should have been. I am really hurt and suddenly feel like these friends aren't as close to me as I thought. My other friend told me not to take it personally, but how would they feel? Any advice on how to move on from this? I'm really upset. -LEFT OUT

DEAR LEFT OUT: It’s funny how social media can make everyone feel like they are back in high school. I’m sorry that you felt left out by your friends. It sounds as though the friend that planned it either didn’t realize it would upset you or was being thoughtless. In any case, your feelings were hurt. I am proud of you for sharing with her how you felt and for being able to express yourself. Don’t take it personally, is my advice to you on this one. Everyone can’t be invited to everything. If you want to spend time with your friend that just got engaged, offer to take her out for dinner or a drink to celebrate — just the two of you. Give your friend who planned the event a pass on this one and then see what happens moving forward. If you find that she continues to leave you out of things, you may need to talk to her again and make it very clear that she is hurting your feelings. If it persists, you may want to take a step back from her and guard yourself. Sometimes our definition of friendship and other people’s are not the same. Show up for the people you love and care about — but remember they need to show up for you, too. 

DEAR NATALIE: My ex and I recently split up and I decided to keep my engagement ring. He is furious because it was a very expensive piece. I should know because I paid for half of it. I caught him cheating and ended things then and there. He doesn't seem that upset about us breaking up, and in fact seems more upset that I won't give up the ring. Who is right here? —THE RING IS MINE

DEAR THE RING IS MINE: I agree with you on this one. Considering that you paid for half of it and he was the one that broke off the engagement by cheating, I would argue that you have a claim to that ring. Some people may disagree -- and depending on the value of the ring you may want to consult an attorney -- but it is really wild to me that he would try to take it back after his actions. Stand your ground. He may give up when he realizes you're not willing to just roll over for him on this issue. Sell the ring, recoup what you can and invest it in something that will bring you stability moving forward. A happy life is truly the best revenge.

Please send your questions to Natalie Bencivenga to

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DEAR NATALIE: I have been friends with “Shawn” for years and we have always had a good relationship. Granted, he deals with some mental health stuff that can make him challenging to be around, but overall, we have always had a nice friendship until recently. He has gotten really weird about women and dating. He claims he has been reading a lot of MGTOW articles online and has started spewing some really nasty stuff about how he feels about women and feminism. I care about him, but I really don’t want to support or enable this behavior. How do I tell him how I feel without alienating him further? As one of his few friends — and as a woman — I feel it is my responsibility to pull him back from the cliff. What do you think? -BACK FROM THE BRINK

DEAR BACK FROM THE BRINK: For those that may not know, MGTOW stands for “Men Going Their Own Way” and from what I have read online, it is a space where men are gathering to discuss anti-feminist thought and engage in seriously misogynistic conversations under the guise of men being marginalized by feminism. It isn’t based in fact, but rather in frustration. There are certain places we can’t follow people and this may be one of them. I’m sorry that your friend is deflecting from his own issues and blaming women. I would give him once chance to hear you out and then walk away. While he is entitled to “feel” a certain way, that doesn’t make it true. By perpetuating stereotypes, falsehoods and harmful information, he is setting up more space for women, girls and femmes to be harmed — or worse. Yes, this rhetoric can and does spill over into real life. If he scoffs at that — and considering where he is emotionally he most likely will — you have two choices: You can either try to “fix” him, which you won’t be able to, or you can walk away. It isn’t your responsibility to pull him back from the brink. I would create a hard boundary for yourself and let him know that until he is willing to engage in rational conversation and recognize other perspectives, there really isn’t a space for him in your life. I know he is your friend, but it will be harder and harder to stay friends with him if he starts spewing hatred towards you. Get out of this dynamic while your mental health is intact. Maybe one day he will recognize what he lost and reach out again with a more open mind. 

DEAR NATALIE: My good friend and her boyfriend just split. They had been dating for about four months and things weren’t working out. I think that because of the pandemic, they just weren’t able to spend enough time together and realized they didn’t have enough in common. They mutually agreed to break up. It’s been about three weeks and her ex has been DMing me, saying that he wants to hang out. I think I might like him, too. I asked my friend if she cared, and she said she didn’t. Then I talked to another mutual friend of ours and she said that my friend is mad that I even asked her about her ex. “He should be off limits,” she said to our mutual friend. What do I do? Should I ask my friend about this? She may just lie to me again and say she never said that. I don’t want her harboring resentment towards me. Is this even worth the hassle? —WHAT ARE THE RULES

DEAR WHAT ARE THE RULES: If you asked your friend and she said she didn’t care, it isn’t really fair of her to go behind your back and say that she actually does care. Her behavior is petty and passive aggressive. I would confront this situation if you really like this guy. Ask your friend to just be honest with you. Tell her that you heard from your mutual friend that she really is hurt by you wanting to date her ex. Some people would say, “Always pick friends over boyfriends!” but I think life is a lot more grey. Each situation warrants its own examination instead of just blanket generalizations. If she feels so strongly about this, then she needs to express that to you. Maybe she was just embarrassed that he moved on quickly. Maybe she was a little jealous that it was with you. Perhaps this breakup wasn’t as “mutual” as she told everyone and now is feeling insecure. Give it time and space. If this guy really likes you, can he wait a little longer to let everything calm down around you? Can you respect where she may be coming from and meet her halfway on this? Can you handle the fact that she may not give you her blessing? Weigh this out. What is worth more to you in the end? I can’t tell you what to do, but I would think long and hard about my friendship and whether or not it is worth putting it in jeopardy for a potential romance.

Please send your questions to Natalie Bencivenga to

asknatalieadvice@gmail.com. Follow her on Twitter

@NatalieBenci and on Instagram @NatalieBenci