Nov. 23, 2025

DeAnna’s Dating Dilemma

DeAnna’s Dating Dilemma

Should you date someone in the friend group?

DeAnna gives all the details to Kathy on why she’s feeling conflicted when it comes to a prospective date.

See omnystudio.com/listener for privacy information.

00:00:00
Speaker 1: iHeart podcasts bring you the ultimate summer of love tree.

00:00:04
Speaker 2: This is Famously Available. Hi, it's Kathy Schwartz.

00:00:09
Speaker 1: And I'm Deanna Stagliano and.

00:00:11
Speaker 2: We are back with Famously Available and we are just getting ready to dive back into all things about dating with some more girl chat.

00:00:19
Speaker 1: All right, So I know we're all going to be at jingle Ball. You're going to be there. You've had the pleasure of already seeing me go on one date.

00:00:25
Speaker 2: I got to tell you that looked so I'm I don't know even at my age. You put a man in front of me and let me talk to him for five minutes. When I see his eyes and his smile, I can tell you whether I'm interested in the second day. That's how quickly I can do it. But it was painful to watch you because you clear in my mind you clearly were not interested in that date that you had.

00:00:51
Speaker 1: Well, I won't I won't go back because we already did a podcast over that. But I think you're right, Kathy. I think I realized pretty early on. It also was a It was also was a weird scenario, you know what I mean. It's not like it's like you go out to dinner with one guy and get to yeah, you know what I mean, different scenario, like all the friends were there who were right, Which is why I'm also I feel a little apprehensive now about bringing this one because he's okay. No one on the podcast introduced me to him. He's somebody that I met myself. A lot of our friends do not know that we have been seeing each other. So then to bring him to such a public event.

00:01:26
Speaker 2: Well but it's well, it's not going to be. I don't think you and he would be on camera. I just had a brilliant idea. This is Kathy, this is my min mind works. You bring him, and you bring him, and you know, we don't nobody don't know who he is. We won't put one camera, we won't say his name. And then they can reach out to the East Coast guy and ask him if he wants to come and have a second date with me, a third date I guess would be and then if he isn't nice to me, you all could torture him.

00:01:57
Speaker 1: No, we're not bringing him back, Kathy, because you're worth more than what he gave. You are worth more than what he gave to you. We're not bringing him back. I'm not even going to stand for it because now I have a tainted little taste in my mouth for him. So we can't have him back. We need to set you up with someone fresh and new.

00:02:12
Speaker 2: Are you? Have you been doing dating apps?

00:02:16
Speaker 1: I did dating apps, I guess about a year ago. I haven't been on them in over a year. Okay, it's a show, don't do it.

00:02:23
Speaker 2: Wait, wait, I have to tell you. I don't know if you know this, but Joan and Susan and Nancy, all from my season with Golden Bats for one, all came to Austin like three weeks ago.

00:02:33
Speaker 1: I saw.

00:02:34
Speaker 2: Okay, we had a blast. But one of the things, uh, Susan and Joan were harassing Nancy and me. You've got to get on a dating site. I said, guys, it's brutal. It is brutal, and Nancy's younger than I am, and it's still brutal. So just you know, one too many glasses of wine, and we said, we said uncle. We got on and then we spent the rest of night going really all literally. We took turns holding up guys pictures that were fifty pounds overweight, holding up dead fish with bear cans, ball caps backwards, you know, ridiculous, or thirty year olds that said, hey, you know you do want to be my baby mama. I mean, it was the whole thing. We died laughing. It is. So, I do not think that online dating works.

00:03:21
Speaker 1: So here's the thing. I did do it for a period of time. I did go on a few dates. One guy I dated off and on for about a year and a half, off and on. Wow, I did date another guy who I still keep in touch with to this day, who's he's super nice. You know, Yeah, I think it can be good. But I am with you, Kathy, where I would really like to meet someone the old fashioned way, And I would say in my age group in particular, what I found from the dating apps were just a bunch of men who wanted to have sex. That's all it was. Yeah, men these days are so quick to send you pictures of their private parts they fast forward, or you just get the ones who aren't real and just want to message you for a month on end.

00:04:03
Speaker 2: Well they really like you to send a check to them for you know.

00:04:07
Speaker 1: Right or that, or it's just some old man who's married at home at diaanes board, you know, what I mean.

00:04:11
Speaker 2: You know, I'm ready for advice on this because honestly, I get out, I have friends, I got, I go out for dinner, I go out to bars, I do. I do a lot of dating. I'll give myself a lot of opportunities to date. But the thing where I need help is how do you how do you meet men organically? I think it's where you could give me some advice because you've been around. I mean I've been around, but I've been married, you know, for a long time too.

00:04:44
Speaker 1: Yeah, I don't know, Kathy. I do believe that you should give the dating apps a shot. I believe that you are putting yourself out there. I also as cuckoo as the sounds like, let everybody call it what it is like. I believe we're all destined for a path, and it may just not be in your path right now. Kathy, you are meant for so something else. You are meant to do all of these things right you did, You did the Gold Baster, then you did Paradise, now you're doing this podcast. You know what I mean? There could be a point in your life that you are destined for more and you are not fully open into a space to have someone. I'm not God. I'm not going to tell you what that is, but these are the things that go on in my twisted mind. Whatever my path is, I just want to be on that.

00:05:22
Speaker 2: Well, let me ask you, do you ever think I mean? I will tell you the thought has crossed my mind that I am. People always accuse me of being friends of friend zoning men. I don't think I do. But maybe maybe that's maybe that is my path. I don't know, but I know that where I was when I was your age and when I was in my thirties, I wanted that man twenty four to seven. That is something that I'm now thinking about. Do I want a man twenty four to seven? Do I want a man to live with me? Or do I like waking up and reading my book in my bed sometimes till ten in the morning, you know, or going to bed and I want to go to bed. But I do think it our age, at my age, a relationship can look differently. Do you feel like it ken at your age or not?

00:06:09
Speaker 1: Absolutely? And I've shared this multiple multiple times on the podcast. Is that I A. I don't know. I definitely don't want more children. B. I don't know that I want marriage and also seeing like I don't know that I want to cohabitate.

00:06:22
Speaker 2: With anyone permanently or at all.

00:06:24
Speaker 1: I don't know. I'm really on the fence about that.

00:06:26
Speaker 2: See I would cohabitate. I don't think I need to live with someone full time. Susan from our show, you know she has a long distance boyfriend. I think that's I don't think I could do that. Like, I know the parameters that I have. I if I dated a guy that's in California, I would jump in that. I'm sorry, I have to rewind my brain. Gary Teresa, Joan and Chalk and mel and Peg three couples who to this. I mean one's divorced. But the issue is always around living in the same town and moving, and I actually don't have that issue. I would move wherever, and then I would come back, keep my home here and go back and forth. I think what I'm trying to say is I am much more flexible now because I don't have children at home like you do. I would think i'd be. But here's the rub. And I was talking to my guy friend about this the other day. He said, well, maybe you're just looking for friends with benefits. I said no, no, no, I want the commitment I want, but it doesn't mean I have to spend twenty four seven with you. It doesn't mean I want you to live in Paris and I'm living in Texas. But I feel like I'm so open to an evolved relationship because my kids are grown, because I'm retired, and I don't know if you're in that space or not. Well, obviously you're not tired. I'm saying, I don't know if you're in the space of looking at a relationship differently than you marriage.

00:08:01
Speaker 1: Here's the thing I have been struggling with this as I've been dipping my toe back into dating because I'm so used to. Obviously, I was with my ex husband for over fifteen years, right, that's a long time. It's a large chunk of my life. I find personally that as women, we are raised and in our generation, it was you find a man, you take care of a home, you birthed his babies, you're barefoot and pregnant, and you take care of him.

00:08:34
Speaker 2: That's my generation. You're saying, that's your generation.

00:08:37
Speaker 1: I'm on the cusp of whether that was right or wrong. The matter is, Kathy, I never felt that in my soul. I always wanted more. I did not want to give up the chance to have a career. I wanted a husband. I was on the fence for a while about kids, but I love my children. But I never ever was fully comfortable being him the traditional values of what people interpret the Bible to say, man is the leader of the home, the women is subordinate, and then everything else in line. I never felt really comfortable with that. That's just like, to my core, that's not how it is. That's just not how I feel. That's not the relationship that I want. I do, on the other hand, believe that we are built for partnership and companionship. I do believe in monogamy. I do absolutely believe in that. I believe that the Lord designed us to have partnership, to refine ourselves and be able to live a life with another human being. Now let me get twisted for a second. I also believe we can have many great loves of our life. Right. I have had that young, crazy love, right, that high school sweetheart. I've had that. I loved that man more than like me too. It was the sick part, the butterflies, you know what I mean, That unhealthy love where I was just like I needed him. I couldn't. I couldn't. I had to be with him like it gave me the butterflies, that gave me, the craziness, it gave me all of those things. I've had the mid twenties. Love where I was really unsure. I've had that when I met my ex husband, the one that I thought was going to change my life. This one was it. This one was the one the person that I chose to be my partner and have children with. So I am sharing that with you in a sense that like I think this is where I'm getting confused in dating right now, because I don't have that piece when the few people that I have dated to where they come in and they blow me away. But I believe that is because I am different, I have matured. I am in a place in my life just like you that I don't really need a man, do you know what I mean. I don't need the kids, I don't need the diamonds. I can buy them on my own. It is a desire to have someone to share my life with. So therefore I am confusing the two because I have had the opportunity to date some really great guys. The guy that I saw off and on for a year and a half, he was wonderful, and he was emotionally safe and great in bed, all of the wonderful things. But in the long run we did not line up for me what I felt was going to last a period of time.

00:11:10
Speaker 2: This man well so and therein I think that is maybe a difference in age or maybe again I don't know.

00:11:20
Speaker 1: And you have both, Bathy. Can you have someone who's really wonderful, who shows up and devis you an amazing bouquet of flowers, who takes care of you, who takes you out to dinner, who never asked you to pay for a dime, and is also amazing in bed? Or do you have to choose? Do you have to pick one or the other?

00:11:32
Speaker 2: Who knows? But I think maybe again, our experiences to help define who we are. Our past helps define who we are in the present and our future. So I think your situation was very different than mine. I think maybe that's why you're struggling to jump into this, because you don't want to have what you had before, and you see that as a negative, like it was rough, I look at the positive. I don't know for me not that my marriage was perfect. You show me a perfect marriage, and I'll show you two liars. But but I had a good marriage and a great man. Having said that, where I look as is this vessel. I'm an open vessel now, and I'm looking for that person who will walk with me, who will enjoy things with me, because I'm at a time in my life that I can do that. I don't need any more diamonds. I don't need all that. I don't need all the trappings need. I don't need a guy who's living on Social Security alone either. But I'm saying, but Ben asked me that. He said, well, I said, I'm looking for the guy to spend this last great chapter with. He said, why does it have to be one guy? I'll tell you why, because I believe that for me, I'm not interested in serial dating. I'm interested in a monogamous relationship. And if i have a monogamous relationship, I feel like I'm old enough to know when I find the right one, I'll know that he's right because I'm taking all those past experiences I've had into this relationship. And that's why for me, when I go out on a date with a guy, I can tell you very quickly whether there's And that's why this guy East Coast guy, that's why he's still in my head, because I could see a future with him. I could see. It's just you know, timings, everything kind of thing.

00:13:28
Speaker 1: Not the right time, Kathy. Maybe he will pop in and it'll feel right. Maybe now is just not the right time.

00:13:34
Speaker 2: You know what.

00:13:35
Speaker 1: Here's the thing. You're a freaking catch, Kathy, and who am I? And we're at a point in our lives that we do get to be picky, right. We're not trying to have someone's babies, We're not trying to get me here.

00:13:45
Speaker 2: But wait a minute, you're just I've got I gotta call you on this. Danna. I calling you Danna for everybody out there. I call her Dianna because my sister in the last name is Dianna, not Deanna. So now I'm going back to d you. It seemingly have this guy. So what is in your way here?

00:14:01
Speaker 1: I'm in my own way because I think too much, because I don't want to ruin a friendship, because I'm scared about the age difference. I'm in my own way.

00:14:10
Speaker 2: Yeah, won't know unless you jump in and try.

00:14:13
Speaker 1: Here's the thing, he's very patient. I haven't scared him off yet, and I am one thousand percent. Everything that I am telling you are things that I have said to him. I would not be saying anything to you right now that I have not already brought to his attention.

00:14:24
Speaker 2: So if he knows this about you, and he's still willing, he's he's in, I should tell you who he's in. I know. Here's the thing. You you're clearly reticent to jump in with this guy, and you keep saying you don't want to lose the friendship. We started this whole podcast with you going on about all your fabulous friends that you spent and yes, albeit girlfriends. What makes this friendship with him? It's so special that you're afraid to quote unquote risk it.

00:15:03
Speaker 1: I think because we have mutual friends, do you know what I mean? And I am traumatized by a divorce.

00:15:09
Speaker 2: Oh, so could get messy. It's not really the friendship. It could get messy.

00:15:13
Speaker 1: Yeah, you know what. There's so much fallout with divorce, like friends that chose sides, friends that I don't speak to anymore, and those were it wasn't just the loss of my marriage. It was the loss of family, it was a loss of friendship. I grieved on multiple levels. That was so very hard for me. And it's the same thing with this. We have mutual friends, we see each other pretty frequently, and a lot of our mutual friends do not know that we have moved into more of a dating.

00:15:40
Speaker 2: So you see it sort of as a then diagram that we're going to grow trees out of this branches and you don't want to cut off branches.

00:15:47
Speaker 1: And it's all out scares me if it doesn't work out. If I wake up tomorrow and I'm like, ah, man, I don't know your age difference, I'm scared to see you naked, you know what I mean? Like the age difference really gets to me, Like.

00:15:56
Speaker 2: Okay, now you're hetting close to home here. Would you talk about it? I don't know. I will say to you that if that's how you feel, you're always it seems like you're going to find it a reason the next guy you know maybe doesn't know your friends and and you know, I mean.

00:16:15
Speaker 1: Right, or I get to decide that I don't want to. So we said this before. There are lessons and everything. This this man, for whatever reason, is meant to teach me lessons and he has been really wonderful to me.

00:16:26
Speaker 2: He does he live in the same town he does?

00:16:28
Speaker 1: Yeah, yeah, not far from her.

00:16:31
Speaker 2: Yes, seriously, I know, I know, I know.

00:16:34
Speaker 1: He's really great.

00:16:35
Speaker 2: Okay, I need you to bring him to jingle Ball so I can have a little chat with him, because I'm a.

00:16:41
Speaker 1: It terrifies me to bring him around other people. Uh, the judgment from others really terrifies me. Are they going to think he's good enough? Are they going to think he's good looking enough? They? Are they going to think I'm good enough for him?

00:16:52
Speaker 2: Guess what? Guess what matters? Guess what matters? I'm being your mother. What matters is do you think he's good enough for you? And does he think you're good enough for him? It matters what you guys think of each other. That's girl talk. That is girl chat right there, and.

00:17:09
Speaker 1: The same thing to him. You also get to decide this is not a one way street.

00:17:13
Speaker 2: He did decide, Dary, He has decided. So you know, now you're going to have to strap on your big girl boots here and decide, you know, whether or not you're willing to go down the road. But as someone who would love the opportunity of going down the road. I'm saying, not thinking, what the hell is wrong with you?

00:17:31
Speaker 1: Not?

00:17:31
Speaker 2: And there's nothing wrong with you, by the way, with me, Kathy, No, can we be positive here? Can we be positive?

00:17:38
Speaker 1: I say that in the best way.

00:17:40
Speaker 2: Well, we all have issues. But do you have this guy who is sending you flowers, who is calling you, who knows what you do for a living, who is saying I know you, I know all your foibles, I know your children, I know your friends, and I want to go down this road with you. And you're sitting there saying, you know what are you on Aisle one? Are you the guy? And I yeah, but maybe on Aisle six, this guy is standing at the checkout line waiting for you. What you know? You gotta think of that.

00:18:07
Speaker 1: It's me, Kathy, I am holding back. What if it's not all there?

00:18:10
Speaker 2: Right?

00:18:10
Speaker 1: The friendship is really great. We have wonderful conversations.

00:18:12
Speaker 2: I will like, you've already wait, you've already made it a foregone conclusion, which I think is wrong. By the way, that should you date him, Let's go call him Joe Supermarket Joe. We've heard that before. Let's just say you date Joe, and then three months in, you know what, you as an adult and a beautiful, strong woman, and Joe over there can say, you know what, we tried, but we're going to go back to being friends. That's where our lane is, that's where we fit best. And you know what, your other friends are going to support that because they love you and they care about you, so don't I would encourage you to not blame what if this? What if that? You never know unless you go down the road of trying. And a year from now, I hope we're sitting on this podcast and you're saying, I can't believe it worked out. I can't believe you. Remember a year ago, Kathy, when I was saying I was so afraid, you know, to go down that road with him, all of those things. It could be everything you want, all wrapped into one little package. Great sex, great romance, a guy who cares about you, will treat you well, who will love your children, who will do the dishes, He'll bring you coffee in bed, whatever it is your dreams are. He could be just standing there, you know, waiting for you to wake up.

00:19:30
Speaker 1: I know, and it's only I am scared. I am scared. I am one hundred percent scared.

00:19:36
Speaker 2: I am Well, you're the only one that can change you, my darling.

00:19:39
Speaker 1: I know. Do you get all of it? Kathy? Do you get every bit?

00:19:43
Speaker 2: Do you get the we never get every bit? D nobody does?

00:19:46
Speaker 1: Asking you what do I have to figure out? In places where like that's not as important to me?

00:19:51
Speaker 2: Do you get You're like, you'll know you're not even giving him the chance to show you. For example, maybe your thing is and I'm being funny here, but maybe your thing is. I can't stand it when my husband left the dishes on the sink and didn't put him the dishwasher. And now you're with this guy. You're rolling out of bed. You know, he bought you a great Christmas present. You're you're on a week's vacation in Port of Iarta, and you know what, You get home and he leaves the dishes in the sink and you'll sit there laugh and why did ever think that was such a big thing? Because he'll give you enough of everything else you want. I'm trying to get you to think on the positive side here. Stop looking for pitfall, Stop looking for the train wreck that isn't there. Let me ask you have you kissed him yet?

00:20:37
Speaker 1: I have it?

00:20:38
Speaker 2: Can he kiss Yeah? It's good?

00:20:42
Speaker 1: Yeah, yeah it was good.

00:20:43
Speaker 2: Well, you know what if his kissing's good, as you move down, he's probably just fine. I mean, give it a chance. I want you to give it a chance. You know, there's a lot of fish in the CD, but a lot of them are carp and you know you found this beautiful eel stare. I mean, I'm trying to think of a pretty fish. You know. He's standing there saying come on, come on, and you're sitting here giving me a thousand reasons why you shouldn't try. I'm saying, you only have one reason to try.

00:21:15
Speaker 1: I do many things. Well. I can do this and put my life out there and be really vulnerable, really well to a bunch of people who I don't know who are listening to our podcast. I can do it with you in the most intimate places in my life. The walls are really thick. Those are the hardest ones to come down. I can be open and honest with you and go on a television show and do a podcast and do all of that and be true to myself and all of those aspects. But then you put me in a situation where exactly what I am hoping for shows up and the walls are so thick because I'm really scared. I'm really really scared.

00:21:56
Speaker 2: Let's reverse the tables here for a second. What I this for me? What if the tables returned and I was saying, de I met this guy, he said in the most gorgeou boy I'm gonna put out. I'm putting this out at the university of it happens. I met this great guy. He's a great kisser. He's a little bit. He's twelve years younger than I am. Let's just yeah, he's twelve years younger. But he sent me flowers. He loves me. We have mutual friends. But I'm so afraid. What would you tell me to do?

00:22:23
Speaker 1: I would tell you to go for it.

00:22:24
Speaker 2: Hello, I know, get that beautiful mirror, mirror on the wall, look at it and say I can do this because the upside potential D is amazing. Like this is what By the way, this is what women do. I think, which makes women's friendships different from men's. I think I am supporting you because I think you are a lovely kind you have so much to offer, and I'm encouraging you to go down this road and be vulnerable because this may be the guy at the checkout stand. You know he may be, and if you don't take the risk, you're never going to know. And so thank you, Kathy.

00:23:06
Speaker 1: It is easy for me, as my friend to take those compliments. It is easy for me. It is easy for me to project that and say I know that I'm a real catch. It is not easy for me in an intimate relationship like that, to accept that, to allow someone to treat me.

00:23:22
Speaker 2: We are going to continue working on that, because you know what it's getting to be. The end of the year twenty twenty six is around the corner. Do you have any New Year's resolutions?

00:23:32
Speaker 1: No, I don't do resolutions, and I have welcomed a new year. I have been ready to wash the last year off of me, let it be gone. I am welcoming a new year. I believe that I am as close to my path as my soul's purpose is supposed to be.

00:23:46
Speaker 2: Well, you're going to get closer if that guy comes to the jingle ball. I'm going to make sure of it. But it's funny you say that I don't have any resolutions. I just hope that this has been a great year for me, even though I haven't, you know, found the person that's going to walk with me down that Sunnybrook road. But I've had lots of great experiences, and that's what I want in twenty twenty six. And I think what I realized with each passing year. It's on me to make every year great, every day great. I can't rely on somebody else. I don't rely on my kids or my friends. I look to myself to make my days and my year's the best they can be.

00:24:28
Speaker 1: You're freaking catch, Kathy, Well, so are you. It's in the cards for both of us. You are a freaking catch. We are a freaking catch.

00:24:35
Speaker 2: Well, I think the king in the deck has found you.

00:24:38
Speaker 1: So well, let's not put the car before the horse. Okay, everybody slow down. We'll see if I bring him to Jingo bol.

00:24:44
Speaker 2: Or not keed. All right, So, so tell me what you want in the new year. I know you don't make resolutions, but tell me tell me. What I would like to see happen to be in the new year is finish that sentence.

00:24:58
Speaker 1: What I would like to see to me in the new year is peace. I would like peace in my life. I am tired of the highs and I am tired of lows. I want to finally, for the first time in my life, be riding at a level pace that's never happened for me ever.

00:25:14
Speaker 2: Wow, No, yeah, I think for me what I want in the new year is continued good health and opportunities to just keep enjoying life and obviously you know, finding that person, but just keep having experiences that where I can, I can want be a One of the things that I've liked in last year is people coming up to me and saying I've given them hope. I like being that beacon of light that shows people who are golden that there is life after sixty, there is life after seventy. So I want to keep doing that. My wish is for you. I'm going to tell you what my wish for you is that you will find a way to calm the fear in your brain and take some good risks for yourself.

00:26:05
Speaker 1: Thanks, Kathy, I love you.

00:26:07
Speaker 2: I love you too.

00:26:08
Speaker 1: I'm looking forward to seeing you in a couple of weeks when we are on a date together with someone else.

00:26:15
Speaker 2: Well, you and one thing I can be sure of you and I are not going on a date, but.

00:26:21
Speaker 1: We don't have a romantic relationship, but we get to be friends the best time ever.

00:26:25
Speaker 2: You're right and I wish you a very happy Thanksgiving you and your family, and I cannot wait to see at jingle Ball.

00:26:32
Speaker 1: Me too, Kathy. This is so wonderful to see you. Happy Thanksgiving.

00:26:36
Speaker 2: Love, Thanks Weedie