Trigger Warning: This article includes discussion of sexual assault.
Is 23 too young to be cynical about dating? I kind of thought so, but the idea has absolutely terrified me for a very long time. After an absurd amount of over-analyzing and self-reflection, I realized it’s likely partly because of relationship trauma (both firsthand and what I’ve witnessed people I care about go through) and partly because of confidence issues. Plus, I haven’t felt any sort of a void in my life because of the amazing friends, family, and career I invest in daily. Still, as I’ve opened myself back up to the idea of dating—for the first time as a “real adult”—I realized I have no idea what I’m doing
Who pays for the meal? What do I wear? Do I hug them when I meet them? What the heck do I talk about? What if it’s awkward? What if I spill something? What if my date wants to kiss me and I don’t want to? What if I find someone I really, REALLY like and they don’t like me? What if someone likes me and I don’t like them back?
The stress surrounding potentially putting myself out there made me wonder if either, a) I was not ready for it, or b) if these types of questions are going to be part of the dating game forever.
After sitting down with 5 different women—each in a different decade of life (20s, 30s, 40s, 50s, and 60-ish)—I found out more about how dating changes throughout life … and all the ways it stays the same.
While these women will remain nameless, a glimpse into each of their lives will help set the scene for their responses:
Where do you typically meet people you go on dates with?
20s: “School, definitely at the gym, sometimes but rarely on dating apps, or through friends.”
30s: “Just dating apps—Bumble, Hinge, Match, and recently Facebook dating—these days. I’ve never had true ‘success’ from a dating app. I’ve been seeing someone from a dating app since September, but it’s still really tricky. Back in the day I’d go out to the bars, but that was not the time guys were looking to settle down. Your 30s are so hard to date. I will say to my friends, ‘Let me know if you know someone!’ and they’ll be like, ‘I know one single person,’ or, ’I know someone who is separated but not divorced.’”
40s: “Bumble. I used to be super anti-app, but realistically thinking about how you’re going to meet someone in your 40s, and in COVID, I thought, ‘Why don’t I just do the easy answer?’ I like that the woman is in control on Bumble and there are lots of safety features.”
50s: “Online dating – I met my current significant other on Match.com.”
60-ish: “My friends usually fix me up with someone. I did online for a month and thought, ‘Blah.’”
When you go on a first date, what do you usually do?
20s: “It’s pretty much always dinner. I feel like there are so many things to learn about someone over dinner!”
30s: “My preference personally is a drink. I hate the idea of a coffee date. I can’t even drink a Diet Coke past noon. I don’t want to drink coffee at 6 p.m. Dinner is a bigger, longer commitment. I also like to do things that are an activity, like Topgolf or something like that. That way it feels less like a job interview, just like the same monotonous questions.”
40s: “Just commit to a drink or a coffee for the first date. One guy took me on his boat for the first date and it lasted hours. I felt trapped and I didn’t want to be on his damn boat anymore. I was like, ‘What was I thinking? How can I get out of this?’”
50s: “Coffee or a drink! You can always choose to go to dinner if it’s going well after. I also think sometimes having a drink (just one, not getting sloppy) helps take the edge off.”
60-ish: “Lunch or a coffee. I don’t suggest drinks because I don’t always want to assume someone drinks.”
What’s a “red flag” or deal-breaker with dates or potential dates?
20s: “If they don’t know how to hold a conversation. There’s a difference between knowing how to talk and converse. If you don’t want to know anything about me and only want to talk about yourself, we’re done.”
30s: “Any dating profile that mentions, ‘I’m into fitness and eating well and into someone who does the same.’ I am someone who has struggled with my weight my entire life, so seeing that is an instant turnoff. It’s so superficial and you can read right through it.”
40s: “When people only want to talk about themselves or seem to only want to text. When someone only wants to talk about themselves, it makes me think, ‘Are you even interested in me or do you just see my face and decide to match with me?’ I also look for someone who is thoughtful when filling out their profile. If you don’t have time to do that, you’re in it for the wrong reasons. A lot of people I’ve matched with seem like they just want to text and text and text and never meet up. I think maybe they just need attention. I’ll usually give someone a couple days to try to make plans to go on a date before I cut them off.”
50s: “I personally wouldn’t go out with someone super timid because I’m so outgoing. You can tell if someone doesn’t click with you.”
60-ish: “Someone who has been married/divorced many times, or divorced less than a year when I start seeing them. I’ve had my heart broken a few times because I’ve fallen for guys who weren’t ready to be fully invested in a relationship because they were not divorced for long.”
“I hate the idea of a coffee date. I can’t even drink a Diet Coke past noon.”
What’s a green flag/turn-on for you on a date?
20s: “My mom always told me to be interested, not interesting. I try to reflect that in dating, but I also look for it. If I can tell a guy is genuinely interested in getting to know me, that’s huge.”
“Also, with the person I’m with now, when I started seeing him, it didn’t feel like trial and error. I could sense that we were both into each other and that wasn’t going to change. It’s just a feeling that’s like, ‘This is easy. This is right.’”
30s: “I’m very confident and know what I bring to the table. I look for that same confidence or mentality. I want someone with a plan.”
40s: “You can tell if you click with someone just by the conversation. After being on a few dates with different people, I can also tell if someone is legit pretty easily.”
50s: “Sense of humor is key for me, truly. I also like when someone asks to kiss me the first time. It shows they respect me and boundaries. Something fun I’m experiencing now is chemistry. It’s a pretty cool thing. When you have that, it’s very natural.”
60-ish: “My faith is important to me, so I like when someone’s values are in line with mine.”
How has dating changed between your first few relationships and the decade you’re in now?
20s: “Guys are a lot more mature when it comes to dating than they were in high school or college. You notice them pursuing you a bit more and taking charge. They offer ideas on what to do. Plus, the conversations are more meaningful.”
30s: “More people are starting to be divorced and have kids now, and earlier on in dating, I kind of shied away from dating people who already had those experiences in their lives. But then I realized I could’ve missed out on great connections with people because I didn’t give them a chance. In recent years, that hasn’t been such a deciding factor up front for me.”
40s: “They say, ‘Love is blind’ … but not this time. After a divorce, you’ve been through such hell. Even if divorce is amicable, it’s still hard to do. Unfortunately, when you date in your 40s, we all have some sort of damage. Someone I went on a coffee date with said, ‘We all have our baggage, but mine is just packed neat and put away.’ Love is no longer blind, and I’m trying to sniff out the red flags early. Ignorance is bliss in your 20s, in your 40s you know there is baggage there, it’s just figuring out how bad it is and if that person has dealt with it?”
50s: “Baggage is going to be there. You and your potential partner both have it now. I’m also way more myself when going on dates at this age. I don’t get nervous anymore. I was getting ready for a date once and I was like, ‘Why am I not nervous?’ I realized I’m way more confident in who I am now than when I was in my 20s. If they like me, they like me. If they don’t, they don’t!”
“Another thing that has changed since I was young is most people are much more established in their careers at this point in life. That gives the freedom for more dates and less financial stress. In terms of exclusivity, when I first started dating, you just kinda knew you were exclusive with someone. There weren’t ‘stages’ like today. It wasn’t until I started dating again after my divorce where I had my very first ‘Are we exclusive?’ conversation with someone.”
60-ish: “The older you get, the more everyone will be divorced. If they’ve never been married, I almost think ‘What’s wrong with them?’ But, I’ve never been married either. So I guess, if they haven’t been married, have they done enough self-reflection to understand why.”
“Another thing is that nowadays, it’s more normal for people to date lots of people. That’s probably because of social media and how it’s easier to meet a bunch of people. I love social media but it can also be a pain.”
What are you looking for out of dating at this point in your life?
20s: “Seeing if someone has a plan or drive is huge for me. My high school relationship had none of that. I know myself and know what I want in the future, and I want someone who also has that drive … and isn’t just all talk—someone actually implementing it. As a girl, I’m always looking into the future, but I also know I have time if I don’t find ‘the one’ right now.”
30s: “I remember being in college and meeting the most amazing guy. We were so in love, but I thought, ‘I don’t want to be 20 years old and dating my future husband.’ When that became a possible reality for me, it scared me. I wasn’t ready for that. I wanted to be independent. When I reached my mid-20s I felt more pressure, and I wasn’t sure if I was ready for that. It wasn’t like, ‘I don’t ever want this.’ It was just ‘I don’t want this right now.’ And then I dated a few people and when those didn’t work out, I looked around and it was like all of a sudden I missed the boat.”
“I dated a guy who said, ‘I don’t feel like I can give you what you want right now.’ But then I responded, ‘When did I ever tell you what I want? You never asked me.’ He said, ‘You just seem like you have it all together (professionally, financially, personally), so I’m assuming you’re looking for a husband.’
“My brother and I go to concerts together and my friends and their spouses ask me to dinner. I’m just looking for someone to go with me to those things. I don’t need a husband right now. And I’m not looking to compromise or settle just to have someone to marry.”
40s: “Someone who within the days that I’m available, wants to be beside me in this thing I call life. I have vacation time and I have income so I can travel. I want a travel companion.”
50s: “Initially, I was looking for someone to do fun things with, but also someone whose faith and values align with mine and is stable, both professionally and personally. Because as much as we want it to be, life can’t be fun every day.”
60-ish: “The biggest thing is a companion. The hard thing for women is that you feel like you are on somewhat of a timeline if you want to have kids. Before 35 is way different than after 35. I’ve been a foster mom and have nieces and nephews, so I have kids in my life. I was never 100% sure if I wanted to be married or have kids. I think if I truly did, I would have, because I’m so success-oriented and any goal I truly want to achieve, I do. Once I was past that point, I took dating less seriously.”
“It used to be, ‘If I date someone for a year and they haven’t said ‘I love you,’ I break it off.’ Now that I’m not necessarily seeing myself getting married, I don’t mind as much if we’re having fun together because it’s not really ‘wasting my time.’ I’m so extroverted and love meeting new people, so now I’ll go out and meet someone as long as there’s no major red flags because if nothing else, it’s a new friend.”
Do you have any dating horror stories?
30s: “Everyone is looking for something different, but I signed up for Hinge and Match because they are supposed to be more serious, less ghosting/hookup-y platforms. Then, a guy I met from one of those apps told me on our second date that he wants to watch his partner have sex with someone else. It was hard to not be cynical for a while after that.”
40s: “One guy I met from a dating app had two truths and a lie on his profile. I figured the lie was, ‘I want world domination’ when it was in fact that he doesn’t own jorts (jean shorts). What kind of a person wants world domination?”
60-ish: “One of my coworkers fixed me up with this super family-oriented guy with a great steady job he had for 30 years. He was cute but not drop-dead gorgeous which is always a good sign for me. Everything was great on paper. We went on a first date, and it was good but not great. We had a second date planned but he called and had to cancel (for a good reason), but then all of a sudden he asked me to send him a picture of me in a swimsuit. I’m in my late 40s at this point; I don’t have a bunch of those just on my phone. Then, he sends me a picture of him nude with only a banjo covering his private parts. I asked, ‘Who took this picture?’ to which he responded, ‘I have a tripod.’”
“Ghosting” is a huge term for the younger generations. If something isn’t working out with someone, how do you prefer it ends?
20s: “Preferably a call at MINIMUM, but I would appreciate an in-person conversation out of respect. It would be okay to ghost if it’s someone I’ve never even FaceTimed.”
30s: “When I was younger, ghosting was more of a thing and there wasn’t accountability. I was pissed when it happened to me, but then I would honestly do the same thing. I wish when it happened to me someone would’ve just been open or honest if they didn’t see it working out. I can usually tell anyway. At the beginning there’s so much happening. If I go on a date with someone and then I don’t hear from them, I know they’re not interested. I will be up-front and say, ‘I noticed we haven’t been talking that much, has your interest changed?’ That gives them an opportunity. You can assume so many things, and I don’t want to go through a day at work stewing about not hearing from someone, so I might as well ask.”
50s: “Honesty is important. You have to say, ‘I think you’re a great person, but I don’t know that we’re for each other.’ I think a phone call is the minimum, but an in-person conversation would be preferred.”
60-ish: “This is one of the hardest things and another reason I quit dating. Because unless both people are equally crazy about each other, it’s either, ‘I’m going to like them more than they like me,’ or, ’I want to get rid of them but I don’t want to hurt their feelings.’”
“Just be honest, even if it hurts someone’s feelings. Do it in person or on the phone at a minimum. I’d say via phone, even via text, is fine if it’s only been 2-3 dates.”
Do you have any advice for someone going on a first date?
20s: “If it’s someone you met through a dating app, Facetime to make sure you’re vibing.”
30s: “Date one feels so much like an interview. There’s too much pressure and anxiety that surrounds it. So unless you’re completely repulsed or grossed out by someone, go out again. At the end of the day, you chose to go out with someone because you liked their personality from all the things you talked about.”
40s: “Go on a couple of dates in the same evening (speed dating). I once met someone at 4 p.m. and then had another date at 6:30 p.m. In your 40s, your time is so precious. If I’m not with my kids or my girlfriends and planned for a certain night to be my date night, screw it, I’m already dolled up!
“For people who have been divorced and want to get back in the dating game, you dated before when you found your first partner. I promise it’s not that scary. You have to let your guard down and trust your judgment. Sometimes you don’t trust your judgment because you ‘didn’t get it right’ the first time, but you have to trust yourself. It’s actually a lot of fun. I have so many single girlfriends dating.
“For people with kids, there is pressure to be a role model for what dating looks like. You have to be careful. If I say I’m going to be home at 10 p.m., I need to be home at 10 p.m. and I don’t need to be stepping inside with lipstick all over my face. I want my kids to respect themselves, so I need to make sure I do, too.”
50s: “Just do it. Life is too short. You get to meet new people and it can be safe. Even if it’s just for something to do. It can be fun! To feel more comfortable, talk on the phone beforehand.”
60-ish: “I don’t let them pick me up on a first date, I’ll meet them. That’s partly for safety, partly also because the end-of-the-night walk to the door or asking, ‘Do you want to come in?’ is always awkward the first time and I’d rather avoid that.”
“Also, my mom wanted me to be independent because of my dad not being dependable, but I think she made me too independent. I didn’t want to depend on anyone. I became financially independent and successful in all areas of life. My niece was living with me, and I could see she wanted to be like me. But I told her, ‘I want you to open your heart and your mind more than I ever did.’ She found a great significant other, and she’s married with two kids now.
“Finally, you have the right to say no at any time. I can guarantee almost every single woman has some sort of story about sexual assault or harassment. I was in a situation where I was with a guy and I didn’t feel like I could say no because I told him he could come over. I put it on myself. But that’s not true. You can say no at any point in time. You don’t owe anyone anything, ever.”
After talking to these women, I saw both their perspectives and pieces of myself reflected in them. I saw in them wisdom they gained both from their relationship history and from growing as individuals.
It helped me realize that baggage is something every single person has, and how someone deals with that baggage and moves forward with life tells more of a story about them and their character than the actual baggage itself.
Dating is scary and messy and fun and exhilarating at all ages of life. While some things change as you age, other things stay the same, and you never stop learning about others and about yourself through the process.
Kylie Stine is Indy Maven’s Community Engagement Manager.
All of our content—including this article—is completely free. However, we’d love if you would please consider supporting our journalism with an Indy Maven membership.
