DEAR NATALIE: Can I date a transgender woman as a cisgender man? I met this beautiful woman recently and we had a great date. I had no idea that she is transgender, but she told me towards the end of the evening. At first, I was taken aback. You would never know to look at her. She’s had surgeries over the years and has completed her transition. While I am attracted to her, I also find myself confused and repulsed. I also worry what my family and friends will think. I have never been in this situation before and not sure how to handle it. We made plans to get together again this weekend. I am not sure if I should break them or see her and tell her what I am feeling. I don’t want her to feel bad, but I am not sure I can date a trans person. What do you think? –DATING IS HARD ENOUGH

DEAR DATING IS HARD ENOUGH: There could be two things at work here. The first thing is – put aside their identity. You stated that you are attracted to her. So why should you deny yourself the opportunity to explore this potential relationship? The second thing is – are you embarrassed or bothered by the fact that you may be attracted to someone who was assigned male at birth? Does this mess with your sense of sexual identity? I would look at that. It’s okay if you are uncomfortable. It’s new to you. And not everyone is going to be able to look beyond the fact that she is a transgender woman. I’m sure this isn’t the first time that she has met someone and they ran the other way because of the societal constraints that weigh down on people. Fear has a way of creeping in and holding people back from new experiences because of how they may be judged. But think of this. Here she is. Standing in her truth. Strong enough to share this fact about herself with you. Willing to be vulnerable and open. Why not grant yourself the same grace and just see where the second or third date may lead? What happens if you let go of any expectations or fears and just see how things progress? And if you just can’t do it, at least let her down gently and don’t ghost her. Let’s show each other the care we would want in return. 

DEAR NATALIE: How can we handle business owners in our community who are causing harm? It recently came to light that the owner of a coffee shop where I live is also the landlord of a number of properties in marginalized communities. He recently served an eviction notice to one home and things became violent. It makes me not want to support the coffee shop because I’m seeing that he is capitalizing on gentrification. I know that his employees need jobs, though, so I don’t blame them. Other people are feeling similarly and I’m curious how to approach a conversation with him. I don’t believe that cancel culture is effective in promoting change and isn’t a way to hold people accountable, so I don’t feel like it makes sense to just blast him on the internet for his sleazy business. What would you do? – SLEAZY BUSINESS GUY

DEAR SLEAZY BUSINESS GUY: My mom does these “one-woman protests” she calls them when she is confronted by business owners she thinks are behaving in unscrupulous ways (both locally and nationally). And I have definitely picked up that habit from her, participating in my own one-woman protests from time to time. And since we live in a capitalistic society, voting with your pocketbook can often be a good way to get someone’s attention towards an issue you may have with how they move in the world. Whether or not they do anything about it is beyond your control. But, if you don’t like the way he conducts business, there is nothing stopping you from boycotting it and loudly sharing with your friends and community members as to why you are doing so. You could also send him a letter detailing why you are boycotting his space so that he understands the impact he is making. He’s free to run his businesses the way he chooses, but you are free to spend your money the way you choose, as well. Hopefully, that can send some kind of message his way. 

Please send your questions to Natalie Bencivenga to

asknatalieadvice@gmail.com.

Check out her new radio show every Saturday from 2-5pm EST on KDKA Radio 1020AM, 100.1FM, stream it on the

Audacy app or at www.kdkaradio.com

Watch her award-winning video series with Pennsylvania Capital Star, Facts Over Fear: www.penncapital-star.com

Follow Natalie on Instagram @NatalieBencivenga

and on TikTok @NatalieBencivenga

DEAR NATALIE: I’m acquaintances with the wife of a politician who has recently come under a lot of heat for his beliefs. She’s something of a public figure, as well, and hasn’t spoken up in opposition or support of what he’s running his mouth about. This is making me really upset, as I feel like she’s on the wrong side of history. Part of me wants to shake her because her husband is so obviously wrong. She has recently been asking me to accompany her to events, but I’m not really comfortable doing that because I don’t want to be publicly associated with them. How can I talk about this with her? I don’t want to miss an opportunity for a good conversation, but part of me wants to fade off into the distance. – LETTING GO

DEAR LETTING GO: What is it that you want to accomplish if you confront her over this issue? The reality is, whatever is being said between them behind closed doors isn’t going to be brought into the public sphere. Like most politicians’ spouses, their job is to stand by their side. It can be unfortunate when someone you admire takes a hard turn away from the values that you ascribed to them. But you are under no obligation to align yourself with her at this moment if it doesn’t feel right. You can just thank her for the invitation when and if she asks you to do things, and let her know that you are busy. If she wants to meet in private to discuss how she feels or how politics is impacting your friendship, then that’s your call. People make their beds. This may be one of those moments where there isn’t a way forward together – at least not right now. 

DEAR NATALIE: Last week I went out to dinner with a friend and saw my business partner on a date with a woman who was not his girlfriend. (I’m pretty sure he doesn’t kiss his female friends). He didn’t see me, and I’m not sure what to do. I’m close with his girlfriend and they’re getting married in six months. I know that she values monogamy. I don’t want to blow up their relationship – or the business we own together – but I don’t want her to find out down the road, and be hurt that I didn’t tell her. Plus, if he’s lying to her, is he lying to me? How can I bring this up to him? – KISS AND TELL

DEAR KISS AND TELL: This is so tricky because there are a lot of different dynamics at work here. Considering you are both friends with her and in business with him, it does raise the issue that if he is willing to lie to her – would he lie or cheat you in your business venture together? There’s no cute way to go about this, so just be blunt. Tell him that you saw him and that he better have a great explanation because it impacts not only your friendship with his girlfriend, but your working relationship, as well. People are impulsive. It may have just been that. But, if he is lying and cheating on her, there’s nothing that will stop him from doing the same in other areas of his life. Better to know what is going on now so you don’t have a big financial mess to clean up down the road. If he’s unhappy, he needs to address that with her, instead of creating drama for you. 

Please send your questions to Natalie Bencivenga to

asknatalieadvice@gmail.com.

Check out her radio show every Saturday from 2-5pm EST on KDKA Radio 1020AM, 100.1FM, stream it on the

Audacy app or at www.kdkaradio.com

Watch her award-winning video series with Pennsylvania Capital Star, Facts Over Fear: www.penncapital-star.com

Follow Natalie on Instagram @NatalieBencivenga

and on TikTok @NatalieBencivenga

DEAR NATALIE: Politics is literally ripping my family apart. My brother and his wife have become more and more “MAGA” over the years. At first, we all accepted it. We recognize that my brother has always been vocal about his beliefs. But there are certain lines you just don’t cross with family. We were at my home for a family dinner that we host once a month to get all of my (six!) siblings and their families together. We have the biggest home, so we always host. Everyone brings food and it’s a great time. My youngest child has recently come out to us as trans. He is using a new name, Jack, and everyone has been incredibly supportive of this. He is 15. If this is how he feels, then we are going to love him for who he is. Jack is an incredibly sweet, kind kid and always was. Everyone loves him. Until this transition, he and my brother got along really well. But my brother won’t even look at him now. He called him an “abomination” at the dinner table. So, my husband threw him and his wife out. It was a terrible scene. Jack, of course, is blaming himself for what happened and is devastated over this. He loves his uncle and doesn’t understand why his uncle suddenly hates him. What do I say to this child? What do I say to my brother who I am furious with? Everyone else in the family agrees with us on this issue. Is there any way to put my family back together? –BROKEN PIECES

DEAR BROKEN PIECES: My heart breaks for your family and especially for Jack. Standing as your authentic self takes a lot of courage. I don’t know if much can truly be done to put this family back together other than time. Unfortunately, extreme beliefs lead to extreme actions. Calling his nephew an “abomination” is something you just can’t take back. Even if your brother were to apologize, the relationship is never going to be what it was. I hope your son has a therapist or someone he can talk to about all of these feelings so that he doesn’t fall into a sense of hopelessness, depression or suicidal ideation. Continue to just support him and love him, which is what you are clearly doing. As for your brother, I would wait a beat before reaching out to him – if you even want to do that. What he did was so hurtful and disrespectful, it may take a long time to recover from it. The reality is, these extremist views push people who buy into them so far into a corner, it’s like they can’t find a way out. An attack on their beliefs becomes an attack on their ego – on their very sense of self. Maybe someday your brother will come around, and I hope for your family’s sake that he does. But if his first words aren’t an apology, I don’t see how you can have any chance for a relationship in the far future. 

DEAR NATALIE: A few years ago, I moved into the city where my mom and brother live. I have a great job and a community of friends but my life is missing romance. I don’t know how to “meet” people. I am really family-oriented and am tired of my family ostracizing me because I don’t have a partner. I want to meet someone who I can eventually start a family with but I don’t want to scare them away by leading with that. How soon is too soon to introduce a new date to my family? I feel like whenever I meet someone new, I end up in a position where I don’t know how to communicate to them that I want to date seriously. What are the questions I should be asking on early dates to get to know if things will work long term? –TIRED OF WAITING

DEAR TIRED OF WAITING: I wish I could say online dating was the answer – and I’m not saying you shouldn’t put yourself out there however you choose – but I wouldn’t put all your eggs in that basket. It sounds as though you have built a strong community around you, so lean into social events and keep an open mind. Ask a few friends that you trust if they have anyone that they could introduce you to. Love always seems to find people when they let go looking for it. As for your family, your worth should not be measured by whether or not you have a partner. Let them know it offends and upsets you when they leave you out. They may not even realize what they are doing. When you do meet someone, take the time you need to see what it is that they want so that you don’t fall for someone who doesn’t share the same vision of the future. Ask questions in a way that provides space for openness, honesty and vulnerability. If you don’t hear what you want to hear, ask yourself if it’s a deal breaker or if you can bend with the wind. When it comes to introducing someone to the family, make sure you’ve had the big conversations first. What do they see for their future in the next five years? Is a family in the mix? Marriage? Living together? What does it look like? Are they career-oriented? Do they expect their partner to be? What are the dynamics? Relationships are a series of compromises, but finding out where you stand with your partner is important before you bring your family in the mix. In the meantime, enjoy your friends and build for yourself a life that brings you contentment. A partner will then be icing on the cake. 

Please send your questions to Natalie Bencivenga to

asknatalieadvice@gmail.com.

Check out her radio show every Saturday from 2-5pm EST on KDKA Radio 1020AM, 100.1FM, stream it on the

Audacy app or at www.kdkaradio.com

Watch her award-winning video series with Pennsylvania Capital Star, Facts Over Fear: www.penncapital-star.com

Follow Natalie on Instagram @NatalieBencivenga

and on TikTok @NatalieBencivenga