Top Warning Signs In Dating After 50 | Stylish First Date Outfit Ideas For Women Over 40

Eight red flags when dating over 50. Now, don't worry, you probably follow me if you love fashion, and that's okay because also in this video, along with the eight red flags when dating over 50, I'm gonna be featuring eight fabulous looks perfect for a date night, a girls' night out, or really any fancy event, and you're gonna be going out in the evenings. And of course, everything I am talking about will be linked down below in my description box. Now, make sure you listen to this entire video because red flag number eight was one I was not gonna mention because it's a little bit too personal, but I decided I was going to do it anyway, and I'm gonna be sharing a personal dating story at the end of the video. Mr. Yellowstone's ex-girlfriend actually reached out to me on Facebook, and we had a conversation, and I will tell y'all exactly what I said to her and what she said to me at the end of the video. Okay, red flag number one is when you're on a date with somebody in the very beginning stages or really any time, they say to you that their wife or their ex-girlfriend or their ex-wife, hopefully they don't say their wife because obviously that would be a red flag if someone is married and you're dating them, but if they call their ex-girlfriend or ex-wife crazy, that is a red flag, or if they call their mother crazy, that is a red flag because basically what they're doing is they're not taking ownership of like maybe a part that they played in it, and they're just blaming everything on the ex. I had two people do that in my dating life. I've been dating for two years. I've been on probably 30 to 40 first dates. I've had a few short-term relationships in two of the guys that I dated that were probably the most toxic. Both of them called their mothers and their exes crazy or even narcissistic on the first date, so definitely that is a red flag. So this is look number one that would be so fabulous for a date night. I love this ivory bomber jacket. It has some really cool like sort of coppery-looking buttons on it. It's very like fashion-forward because bomber jackets are a huge trend in 2025. I paired it with these fabulous gray jeans, and gray denim is another huge denim trend we are seeing in 2025. These are by Redone. They're a high-waisted straight-leg denim silhouette. This is a very edgy look, but also very fashion-forward, perfect, like I said, for a date night or a girls' night out. Red flag number two is if somebody tries to move too fast too quickly. Now, I've had this happen to me as well in two short-term relationships. Both of them lasted about six weeks. One was Mr. Yellowstone, and one was Mr. Fitness Guy. After date three, they were already asking me to be exclusive, to not see any other people, and this really comes from a deep sort of insecurity that they really wanna be chosen, and it was almost like they were wanting to see what I would say, not that they really wanted to choose me, but they really just wanted to see if I would choose them, so that is a red flag. What I should have said looking back, because I didn't, I actually said, okay, I will be exclusive with you. I will be your girlfriend, and I ended up ending things with both of those guys three weeks later because the more I got to know them, I realized this person is not a match with me energetically. They're not aligned with my values, and so what I should have said is, you know what? I'm not ready to be your girlfriend yet because I don't know you yet. I've only known you for three weeks, so hindsight is always 20-20, so lesson learned moving forward, you or me, we should not rush into these relationships. We should allow the men to show us who they are consistently over time because that's the only way you're gonna understand if someone is really liking you for you and to have a long-term relationship with you or if they're just in it for the short-term, they just wanna sleep with you, they just want your body, or what have you. So this is another great denim date night look. This is a really cool gray bomber jacket. Now, I did feature the burgundy version of this jacket a few months ago, and I love it, and I was so excited when I saw that they came out with the gray version. This jacket also comes in ivory, and trust me when I say it kinda reminds me of like a really premium designer jacket, like a Balmain or a Kate jacket, but because it isn't by a premium designer, it's a fraction of the price, and trust me, it looks way more expensive than it really is. Every time I wear this jacket or the burgundy one, I always get stopped on the street and like people saying, oh my gosh, where did you get that jacket? I have to have it, so love this jacket. I'll definitely be wearing it a ton this spring and summer. I paired it with my favorite baby flare girlfriend denim jeans. These are a high-waisted baby flare with a floor-skimming hemline, which means they're gonna make your legs look miles long. And then this is a new belt I just got. This one is by Madewell. It has a silver buckle. It's just a thin, classic, timeless ivory belt. I think adding a belt is just a great way to elevate all of your looks, and I love the fact that this one is under $100. Now, if you wanna look like you hired a stylist, but you don't wanna pay them money to hire a stylist, definitely hit subscribe, subscribe to my channel, watch my videos, because here on my channel, I will not only teach you to dress better, I will also teach you to increase your confidence, because it's been scientifically proven that when you dress better, you feel better, and when you feel better, you're going to exude confidence, and I promise you, your life will get better in all areas. So I publish two new videos every week, and I would really love it if you would subscribe. All right, red flag number three is if you meet somebody and they haven't been single long enough. So for me, it's like you have to have been divorced at least one year, and you have to have been broken up with your girlfriend at least six months, because the two times that I have dated guys that have broken up with their girlfriends within the last two months, within the last even six weeks, it's too soon, and they're not over their ex-girlfriend or ex-wife yet. I never have done that with an ex-wife, but I have done it with ex-girlfriends like Mr. Yellowstone. He had only been broken up with her for two months. That was definitely a red flag. I said it out loud to myself, and I ignored it, and I dated him anyway, and it ended up causing me a lot of pain because I had to break up with him six weeks later when I realized he had still been talking to his ex-girlfriend, which more on that at the end of the video. So I think that's just a good rule of thumb that when you're dating somebody, make sure that they have been single for at least a year, especially if it's a marriage, and also have they done work on themselves. I love to ask the question, what did you learn most in your previous marriage? What did you learn from your divorce? If they say nothing, if they say they haven't learned anything, and they really haven't self-reflected, that is a red flag because you wanna meet a man who actually self-reflects and takes responsibility for his part in their failed relationship. Okay, this is a beautiful Michael Starrs dress, perfect for a date night or girls' night out. It's very reasonably prized. I love the fact that it's cut in at the shoulders, so it is very tastefully sexy, and ladies, our shoulders are a part of our body that no matter what your size, they're gonna look sexy and fabulous and amazing. So love this dress. It's very comfortable. It's got a little bit of ruching around your waistline, so it does a great job of sort of camouflaging any of those challenge areas. I love the side slit, and I just think that navy blue is a very classic and elegant color, perfect to wear all year round. All right, red flag number four, inconsistent communication. What does this mean? This means that in the beginning of the relationship, they're texting you all the time, they're calling you all the time, and then all of a sudden, you don't hear from the guy for two or three days, and then they pop back up in a few days and say, hey, what's up, how are you? So here's my response when that happens because this happened with Mr. Neighbor Boy, who was a guy I dated, not really dated, but sort of had a situationship with for like nine months, too long, I know, but that's only because he lived two doors down, and I kept running into him. But what I would say to him is, hey, I really value consistent communication, and if that's not something you can do, I don't think we're a good match. Like, I love being kind and direct right off the bat because that gives them the knowledge to know, like, this is my standard, I'm not the type of girl that's gonna play the cool girl, and if that runs you off, then hey, even better, because I don't wanna waste my time on a man who isn't gonna show up for me and give me consistent communication over time. So anybody who's hot and cold in the beginning, kick them to the curb, they're not worth it. So this is a fabulous burgundy faux fur jacket. I love this jacket. Again, faux fur is super glamorous, and I really adore this color. It's soft and easy. I paired it over this really beautiful burgundy sheer top, so I love doing a top and a jacket of the same color. I think that's a great no-fail outfit formula that you can use, and it's gonna work for you every single time. And then I went with my black Veronica Beard leather flares. I love these pants. They are a high-waisted, floor-skimming hemline. Again, the perfect formula for looking taller and slimmer. If I had to pick one pair of black pants that are like the most slimming pants in my closet, it would be these. I've worn them a ton. I've talked about them multiple times on my channel because they are that good. All right, red flag number five, and that is not planning dates. So if you're in the beginning stages of talking to a guy, maybe you've gone on one date with him, maybe two dates, and then all of a sudden they stop planning dates and they just like text you late at night, or just like every once in a while, and they just wanna come over, but they don't wanna plan dates, no, this guy is not into you. He only wants to sleep with you. And this, again, was Mr. Neighbor Guy that I had this situationship with, right? He took me on two dates, and then all of a sudden he stopped asking me to go on dates and he would just be like, hey, can I pop over? And I made the mistake in the beginning of letting him do that, and then I realized, wait a second, this guy doesn't wanna date me anymore. He just wants to sleep with me. So that's when I cut it off and I blocked him and said no more because I could totally tell if a guy is not planning dates, if a guy is not asking you out, I'm sorry, this might be a hard truth, but it just means he's not that into you and he doesn't want to. So respect yourself enough, and if that's what you want, if you want a guy who wants to date you, of course, and choose you, then don't allow a guy like that to stay in your life because when you block somebody, when you remove somebody from your life, that isn't good for you. What you're doing is you're making room for the right person to come along. So this is one of my favorite date night looks. This is a burgundy sweater dress with a matching burgundy velvet blazer. This would be so fabulous to wear on Valentine's if you have a date, or even for like a Galentine's night out. I love this dress. Under $100, it comes in several different colors. It's wrinkle-free. It is super flattering. I love the front sexy slit, and then this blazer's actually by Mango, so it looks way more expensive than it really is, and velvet is the one material you can wear, and you can be guaranteed to always look expensive and luxurious. Another way to style that fabulous burgundy blazer is with a faux leather bodysuit in some fabulous edgy faded black denim. So these jeans are by A Gold E. They were the number one sellers on my blog last year. They are that good. I have them in two washes because they're so flattering. A high-waisted straight leg denim silhouette. I couldn't live without these jeans, and if I was gonna go on a date tonight, this is exactly what I would wear because I personally love wearing denim on a first date because I think like wearing a dress is almost like trying too hard, but denim is sort of a sophisticated and classy way to be like tastefully sexy and look really fabulous, but you're also looking like you didn't really try that hard. All right, red flag number six is they're not able to hold space for you to talk about your feelings. In the beginning stages of dating, yes, you should keep it light, you should have fun, but if something comes up and you get your feelings hurt, which it will because we're both human beings, right? No one's perfect. You need to be able to go to them in a kind and direct way and calm way, say, hey, when you did this, this really hurt my feelings. So for example, when I was dating Mr. Fitness Guy, I can't remember what, I think he snapped at me and just like used a very rude tone of voice with me like early on, and I was gonna ignore it, but then I was like, you know what? I'm actually gonna bring this up to him and tell them that that hurt my feelings, and so I did, and he was very defensive, and the way he reacted to me wasn't in kindness at all. He was basically defensive and basically turned it right around and blame shifted and started telling me something that I did wrong. So that was a huge red flag because how somebody reacts when you're being vulnerable and telling them how you feel is gonna be a really good indicator of how this person is gonna be able to show up later on in the relationship when you have differences because you will. So that was a huge red flag. It caused me a lot of anxiety, which is why I ended up ending that relationship only after six weeks. So this is a fabulous date night look or girls night out. This is an under $100 faux leather red jacket, another great look for Valentine's Day or Valentine's night. I love the fact that this jacket is cropped because it hits right at your waistline, and I know that jackets that hit at the hip line like the regular structured blazer, all those are fantastic and fabulous. I feel like a cropped jacket hitting you at the waistline is 10 times more flattering, again, because it's gonna accentuate your waistline. I paired it with a light wash version of those A Gold E jeans I had on earlier. Love these, again, because of the high waist and the straight leg, extremely flattering. I know these are gonna be my number one wearing jeans in the spring and summer because they're that good. All right, red flag number seven, and this happened to me on date number one. I would say this is like the worst first date I ever had. I met a guy at a bar. I had matched with him on The League, which is a dating app. It's a pretty good dating app, I guess. Matched with him on The League, met him at a bar at El Braco in Dallas. He had already had two drinks prior when he was somewhere else. He got to this place, I think he was on drink number three or four, and I could tell he was kind of tipsy. We get to the dinner table, he proceeds to order two more drinks and tell me that he had been kicked out of church. So yes, that was the worst first date I think I've ever had, and it wasn't just the fact that he had drank too much alcohol and that he was literally drunk. It was also the fact that he was just not in alignment with my energy and I wasn't attracted to him in the least bit. So if a guy drinks a ton on a first date, huge red flag because drinking too much is never, ever, ever a good idea. On a positive note, one of the best first dates I had was with a very classy guy. I really liked him a lot. I was actually dating him last Valentine's and he didn't send me anything for Valentine's and it just kind of fell apart after that. But the one thing that impressed me about him most was that when I got to the date, he was sitting at the bar and he was drinking a club soda. He did not order a drink until I arrived and I ordered my drink and then he ordered one. So that is a green flag, FYI. Now this is another fabulous date night look. One of my new favorite dresses. This is under $100. It's like a sheer mesh dress. It comes with a built-in slip dress. Again, I can't believe it's under $100 and I really adore this gorgeous blue color. So when I do go on a first date in the future, in the near future, I know I probably will, this is exactly what I'll be wearing. I paired it with my new favorite silver heels. These are absolutely stunning. And then this really cool east-west ivory handbag. This handbag reminds me of like a Kate handbag but instead of being $2,000, this one is very reasonably priced. Okay, red flag number six and this one is on me. This is the personal red flag I wasn't gonna say but this is the most important thing in this video. If you don't take any red flag tip from this video, this one definitely the most important. Do not sleep with them too soon. I need to say this to myself. I need to put it on a sticky and put it on my mirror because this is the mistake that I have made occasionally in the past. And here's the reason why you don't do it. And I'm talking to myself as much as I'm talking to you. Because when you do that, basically what happens in the woman's brain is she releases a lot of oxytocin, okay? Oxytocin is the chemical that makes a woman fall in love. So even if this guy isn't amazing, even if this guy is like inconsistent and maybe he drinks a little bit or maybe he's not that respectful or whatever it is, you tend to ignore the red flags if you've already slept with the guy because you become attached to them, your soul is tied to them, and you have all these chemicals going on in your brain like oxytocin and dopamine and serotonin that makes you think, even if you're not, that you're in love with this guy so you ignore the red flags. Maybe you don't ignore them completely but you ignore them longer than you would have had you not slept with the guy. And here's what goes on in the guy's brain when he sleeps with you. He gets a hit of testosterone. Testosterone is not what makes a guy fall in love. Actually, testosterone makes the guy wanna pull away a little bit. So unless he's emotionally attached to you, sleeping with him isn't gonna make him wanna get closer to you. It's actually gonna have the opposite effect and make him wanna create distance between you until he has that emotional connection with you and until he's gotten to know you. So from now on, moving forward, what I'm going to do is wait. Wait at least a couple of months so that this man can show me with consistency over time that he is after me for my heart and my soul and the whole package and not just my body or just to sleep with me. So those are my two cents on that. Let me know if you agree down below in the comments. One more look. This is a fabulous dress under $100. It's a leopard mesh dress. So flattering. I love the ruching. And leopard is the one print you can wear and always, always, always look more expensive. Okay, story time. Let's talk about how Mr. Yellowstone's ex-girlfriend messaged me on Facebook like last week and she said, Heather, I know this is crazy, but would you be willing to talk to me because I think he's lying to me and I just want to hear your side of the story. So you know what? I was like, sure, because I always believe in women sticking together with other women. So I gave her my cell and she called me immediately. So our conversation went like this. I said, well, why don't you tell me your side of the story and then I'll tell you what he told me about you and all of these things. So she basically said that, you know, she had him blocked because he was verbally abusive to her and said things to her and disrespected her in ways that a man has never done before. So that's why she blocked him. And she also said that he told her the reason he broke up with me and that he told me is because he was still in love with her. He said, yes, I told Heather that I was still in love with you and that's why I broke up with her. So two of those things were complete lies, I think, because he didn't tell me that he was still in love with her. Basically, what he did say is he didn't know what he wanted and that he needed to take some time to do some healing. But then he was like, but I still wanna talk to you and I'd really rather just take things slow. And then that's when I came back to him and said, yeah, no, not gonna happen. I don't need to talk to you. We're not taking things slow. Like, I'm done. We're never, I'm never talking to you again. Like, this is over. So he basically lied to her about that. He told me that he had her blocked the whole time and that she was a narcissist and that she cheated on him when in reality, if what she's saying is the truth, is that she had him blocked, which I broke up with him December 30th. So on December 31st, that night, he sent her an email saying, hey, would you please unblock me? I really wanna talk to you. And she said that she did unblock him and that they ended up talking on the phone for several hours on New Year's Eve night. So that really kind of hurt my feelings. She also told me that the entire time we were dating from November 13th until December 30th, he had been emailing her all along trying to get her to unblock him. So needless to say, we hung up the phone and that was that. I was really hurt. I was sad. I cried. It was hard because, you know what? I cared about that guy, of course. Like, as my daughter would say, who's been to grad school and is a therapist now, she'd be like, mom, it would be weird if you weren't crying. Like, that would mean you're either a robot or a sociopath. So I guess it's okay that I got upset. But then I had to switch my mindset and say, you know what? Thank you, God. This is actually a blessing in disguise because that man isn't for me. That man wasn't aligned with me energetically. Our values didn't match. Obviously, he lied to me. How could I ever trust this man again? So actually, I changed it to thank you, God, for removing this man from my life in only six weeks, again, so that I can make room for the right man to come along because I have no doubt that my Prince Charming is on his way and when the time is right, God will send him to me. So let me know what you think about this video. Did you like this dating advice? Do you like this? I'm not gonna be doing this every single week. I'm gonna be doing this, you know, every so often. If not, if this isn't your favorite, that's okay too. Let me know what videos you would like to see because I am here to serve you. And if no one has told you yet today, I love you. You are beautiful and amazing just the way you are. For more style information, you can head over to my blog, SewHeather.com and on Instagram, I'm SewHeatherBlog. I hope you have a fabulous day. Bye-bye.