25 Success Stories: What Turned A First Date Into A Second
The responses were varied, heartwarming, and sometimes downright surprising.
Dating can be a whirlwind of emotions, ranging from excitement to anxiety. Sometimes, a single moment or a few well-chosen words can tip the scales in favor of a second date. Recently, a Reddit user posed an intriguing question: “What is something your date did or said that made you go ‘I’m definitely going on another date with this person’?”
The responses were varied, heartwarming, and sometimes downright surprising. Here are some of the most compelling answers.
Image source: iaspiretobeclever, cottonbro studio/Pexels (not the actual photo)
Most men hide their sad back story or any vulnerable parts of themselves, but he opened up about being orphaned and his mother's mental illness and how he manages without support and 3 hours later I didn't want to leave the table. His confidence in being honest was so hot. It didn't come across like a sob story.
Image source: Elfprincess, Leah Newhouse/Pexels (not the actual photo)
I am a professional historian. I mentioned Roman toilets and we had a long conversation about them, because he is a history buff too. That’s how I knew he was the one! Together for 3 years. Just got engaged two weeks ago.
Image source: yarnwonder, Josh Willink/Pexels (not the actual photo)
He came up to me, introduced himself and told me he’d marry me one day. Apparently he’d had a premonition on the way to the pub that he would meet his wife. No idea who she was. Honestly I thought he was mental, but he was just so confident about it. Not cocky, just sure that he was right. We’ll be together for 18 years this year and he’s still my favourite person. We laugh daily and he’s my biggest cheerleader.
Image source: KitCat161, Farzin Yarahmadi/Pexels (not the actual photo)
On our first date he stopped while walking to pet a strangers dog, it had me hooked.
Image source: WendigoSlinky, Andrew Neel/Pexels (not the actual photo)
Oh this one is gonna be good, I was on a date with a girl I liked and I got a ping on discord from the boys asking if I can join online, as I’m typing to explaining I can’t she grabs my wrist and tells me no wait one moment, then walks out and comes back with a gaming laptop. I knew then and there. 3 years later we are now happily married.
Image source: madeyemary, jacky xing/Pexels (not the actual photo)
I used to think this kind of thing was dorky, but he wanted to drive me to my car even though it wasn't far at all. Then when he dropped me off, he asked if he could kiss me. I'd literally never been asked that before (I was 35!) and it floored me how endearing it was in the moment.
He is still just as sweet and considerate. We are 2 years strong and expecting our first baby. I really, really love this man. ?.
Image source: fiddledoctor, Budgeron Bach/Pexels (not the actual photo)
For our first date, we got coffee and walked around a Barnes & Nobles for a little while. We were browsing some books by the entrance when a bus pulled up and an elderly man with a walker stepped off. I saw him struggling to open the door and took a step to help. My date, who’s back was to the entrance, whirled around and BOUNDED over to the door, holding both sets open and helping the man through. We’ve been together for over five years now <3.
Image source: Cannabis_Mermaid, Ketut Subiyanto/Pexels (not the actual photo)
I had gotten out of a pretty emotionally/mentally/controlling abusive relationship at the time. So needless to say, I had some apprehension putting myself out there, again. The thought of being vulnerable to someone again was scary.
We spent maybe 30 minutes to an hour at the restaurant. The remaining 5 hours of our date was spent talking in the car about anything and everything. By the time we both (begrudgingly) parted ways for the night, we had a breakfast date planned for the next morning, and it felt like I had known this man for years. It was the first time in a long time that I was able to fully relax around a guy, especially on a first date. So it wasn't anything specifically that was said or done, it was just the way we opened up so easily to each other, even about insecurities, past relationships, etc. He just made me feel...comfortable.
We're coming up on our one year anniversary here in a few days. The road hasn't been completely smooth, as the first healthy relationship after an abusive one can be pretty rough when you've experienced/learned nothing but toxic coping mechanisms and have to unlearn them. But man, I think this is the first time I can truly say I know what it feels like to be loved by a partner fully.
Image source: Scorponok_rules, Vija Rindo Pratama/Pexels (not the actual photo)
It just felt right being together after about 5 minutes into the date.
It's been 13 years since that first date and the feeling still hasn't changed.
Image source: romeosgal214, Viktoria Slowikowska/Pexels (not the actual photo)
He gave me flowers that he picked and tied a bow around, then took my hand to lead me into the restaurant. We’ll be married 14 years in October.
Image source: azninvasion2000, Jep Gambardella/Pexels (not the actual photo)
She insisted on paying for dinner, then busted out a mini travel backgammon set from her purse and asked if I knew how to play.
Image source: brsb5, Breakingpic/Pexels (not the actual photo)
1985, he liked rock music, I like country music. He borrows The Judds cassette from his brother and has it playing when we get in the car. Been married 36 years.
Image source: Available-Line-4136, Tima Miroshnichenko/Pexels (not the actual photo)
She yelled at some teenagers to be quiet in the movie theater. We are married now.
Image source: HatefulTwon, Edward Eyer/Pexels (not the actual photo)
This girl I was dating a few years ago did an impression of a T Rex on our third date, and she went ALL OUT. Little arms at her chest, big dino steps, full effort roar. I knew I'd marry her from that moment.
We got married last summer. We have a little dinosaur on the way this October.
Image source: anon, Min An/Pexels (not the actual photo)
I met a guy on match.com. We talked for a bit and finally met in person. Honestly, I was kind of "meh" on him. He seemed a bit standoffish. We went out to dinner a restaurant I liked, had a great meal and then he asked if I wanted to go for ice cream. I was like "sure" so we went to a nearby ice cream shop, had some ice cream and talked some more. I was still on the fence about him.
So, we finished our ice cream, it was after 10pm and we were getting ready to head out. He looked at me and said, "I had a really great time tonight and want to see you again. How does 7pm next Saturday sound? I can pick the restaurant this time."
I did admire his directness and figured "Why not?" So, I said yes, we went out the following Saturday and he was like a different person - much more relaxed, chatty and open. I later found out he was a *nervous wreck* on our first date because he really liked me and didn't want to "mess it up" (his words!).
Well, he didn't mess it up. We've been married almost 20 years now and have two great kids. :-).
Image source: eye_snap, Ron Lach/Pexels (not the actual photo)
We were at his home, alone for the first time. His friends called, he was on the phone for a second, then when he hung up he said "I am so sorry, I gotta go, my friends have been drinking and they dont want to drive, I'll go pick them up, I'll drop you off on the way."
We ve been married 10 years now and that was the moment I fell in love.
It might seem silly, but I was really impressed how he didn't hesitate, like of course his friends could count on him, even when he had the house to himself with his date, he was still thinking "my friends need help". And he is mature and responsible, he worried that they might try to drive while drunk.
I thought this is a reliable man who has his priorities right.
And he has proven himself to be exactly that over the years we've been together.
Image source: ariesgeminipisces, Matthias Cooper/Pexels (not the actual photo)
He just made me laugh the kind of laugh where I throw my head back and laugh from my heart and belly. He still makes me laugh like this.
Image source: DianaPrince2020, Tobi/Pexels (not the actual photo)
As we were driving to dinner a car swerved into our lane causing him to have to brake hard, he automatically put his arm out over me. It was something my mother always did. To me, it symbolized an unthinking care and thoughtfulness.
We will be married thirty years this month and he is truly thoughtful, empathetic, and caring. I told him he is simply a good man. That is high praise to me. Nothing better than a genuinely good person.
Image source: kindahipster, cottonbro studio/Pexels (not the actual photo)
I went on a first date with my now husband at 18. I'd been on dates before but they (being teenager dates) were always pretty awkward, even if we liked each other and we're doing fun things.
The thing about this date was that, it was kind of weird and seemed like it shouldn't go well. First, I was waiting outside for him to pick me up. He asked if he should introduce himself to my family, and I said no because I had a bad family situation and it wouldn't be beneficial for anyone to do that, but I thanked him for asking. He immediately was fine and we drove to the restaurant.
I complimented the stickers on his console, they were for some rock bands and looked cool. He thanked me and said normally people just compliment the car because it was a Corvette and didn't like his stickers. I had no idea what kind of car it was and apologized but he said it was fine, the car was a handmedown from his brother so he didn't care about it and liked that I liked them.
We get to the restaurant and I warn him, embarrassed, that I'm a messy eater. I don't mean to be, in fact I try very hard to be careful, but I've always a bit of a disconnect between my hands and mouth, and always end up with a bit of sauce on my shirt (I didn't know it then, but I know now I have ADHD). He said that was cool and wasn't judgy at all, even when my tomato fell off my BLT into my lap, and we laughed about it together.
After a bit of small talk, he said he likes to be direct and of it's ok if he asks more personal questions about what we want out of life and stuff. I was thrilled, I hate the "waiting several dates before talking about serious stuff" thing because it always felt like a waste of time. We talked about religion (none for both) marriage (maybe but not for a while), kids (no for both), life goals (both to find nice, relaxing jobs to make enough to focus on hobbies and some travel), politics (left leaning). We weren't the same in every way though, when it came to hobbies I like reading, movies and crafting. He liked video games, d&d and coding. We both were very interested in the others hobbies as well. I felt really at ease with him, even when I had answers he didn't quite agree with, he was very interested in what I had to say.
When we leave, we had planned to hang out at a park after but it was raining. As we were walking to the car, he paused and said "Ive never kissed someone in rain before". I was blown away at how romantic it felt and we had a perfect, sweet kiss.
We hang out in the car a bit longer before he dropped me back at home. He thanked me for a wonderful time and kissed me again (again sweet and not asking for more). I was giddy, once inside I immediately called my best friend to gush about it. She thought the date sounded weird, but was happy for me. I then said I really wanted to text him *right then* because I liked him so much. My friend was horrified, and said I couldn't text until at least tomorrow and to preferably wait for him, or else I would seem desperate. Literally not 5 minutes late while still talking to her, I get a text from him saying "I think I'm supposed to wait longer before texting, but I couldn't help it, I just wanted to tell you again what a good time I had".
It all felt so magical, not because it looked like something in a movie, but because it looked exactly how I would write a romance for me. 10 years later, we are still incredibly happy together.
Image source: throwaway47138, Lina Kivaka/Pexels (not the actual photo)
The first time my (now ex-, but we were married for 16 years and have kids together and I don't regret it) wife visited my apartment, my one cat that was notorious for disappearing when anybody came over (even the pet sitter who he knew well and liked) promptly jumped on her lap and started purring at her. She had no i idea what to do with cats at the time and said so, but just went with it and they became friends right away. If he thought she was a keeper, who was I to argue with him.
Image source: swordofBarsoom, Stanley Morales/Pexels (not the actual photo)
When we had our first date, it was actually our first time seeing each other in person.
He met me outside of my office right when my shift ended… and literally ran across the street to me with the biggest, brightest smile. He took me in his arms and hugged me so hard that my feet dangled in midair, and in the sweetest and most excited voice he said:
“It’s so nice to finally meet you.”
Ten seconds in and I was COOKED. I loved that he never tried to play it cool or aloof. He never hid that he was happy to see me.
He literally swept me off my feet.
That was three years ago, we’re getting married in October.
Image source: GoramReaver, Lukas/Pexels (not the actual photo)
On our first date, some of her ice cream dripped onto her sleeve. Nonchalantly wiping it up, she told herself, “can’t take me anywhere…”
I smiled. She’s been my wife for 7 years now.
Image source: Any_Assumption_2023, Katerina Holmes/Pexels (not the actual photo)
He quoted my favorite poet, TS Elliot, at the dinner table on out first date. I finished the quote. He stared at me across the table for a stunned moment. I swear that was the very moment we fell in love with each other.
Image source: ginger_ryn, Dziana Hasanbekava/Pexels (not the actual photo)
First date with my partner
i told him i had trauma and cptsd and adhd etc. he asked “what does that mean for you?”
instead of judging, asking probing questions, or ignoring it completely, this man asked me how this impacts my life, in an effort to genuinely understand me and my mind
our 6th anniversary is next month.
Image source: Mushrooming247, Askar Abayev/Pexels (not the actual photo)
He said he couldn’t hang out the next night because he was making dinner for his grandma and mom and aunt.
Definitely a green flag. We have been married for 20 years.
#1
Image source: iaspiretobeclever, cottonbro studio/Pexels (not the actual photo)
Most men hide their sad back story or any vulnerable parts of themselves, but he opened up about being orphaned and his mother's mental illness and how he manages without support and 3 hours later I didn't want to leave the table. His confidence in being honest was so hot. It didn't come across like a sob story.
#2
Image source: Elfprincess, Leah Newhouse/Pexels (not the actual photo)
I am a professional historian. I mentioned Roman toilets and we had a long conversation about them, because he is a history buff too. That’s how I knew he was the one! Together for 3 years. Just got engaged two weeks ago.
#3
Image source: yarnwonder, Josh Willink/Pexels (not the actual photo)
He came up to me, introduced himself and told me he’d marry me one day. Apparently he’d had a premonition on the way to the pub that he would meet his wife. No idea who she was. Honestly I thought he was mental, but he was just so confident about it. Not cocky, just sure that he was right. We’ll be together for 18 years this year and he’s still my favourite person. We laugh daily and he’s my biggest cheerleader.
#4
Image source: KitCat161, Farzin Yarahmadi/Pexels (not the actual photo)
On our first date he stopped while walking to pet a strangers dog, it had me hooked.
#5
Image source: WendigoSlinky, Andrew Neel/Pexels (not the actual photo)
Oh this one is gonna be good, I was on a date with a girl I liked and I got a ping on discord from the boys asking if I can join online, as I’m typing to explaining I can’t she grabs my wrist and tells me no wait one moment, then walks out and comes back with a gaming laptop. I knew then and there. 3 years later we are now happily married.
#6
Image source: madeyemary, jacky xing/Pexels (not the actual photo)
I used to think this kind of thing was dorky, but he wanted to drive me to my car even though it wasn't far at all. Then when he dropped me off, he asked if he could kiss me. I'd literally never been asked that before (I was 35!) and it floored me how endearing it was in the moment.
He is still just as sweet and considerate. We are 2 years strong and expecting our first baby. I really, really love this man. ?.
#7
Image source: fiddledoctor, Budgeron Bach/Pexels (not the actual photo)
For our first date, we got coffee and walked around a Barnes & Nobles for a little while. We were browsing some books by the entrance when a bus pulled up and an elderly man with a walker stepped off. I saw him struggling to open the door and took a step to help. My date, who’s back was to the entrance, whirled around and BOUNDED over to the door, holding both sets open and helping the man through. We’ve been together for over five years now <3.
#8
Image source: Cannabis_Mermaid, Ketut Subiyanto/Pexels (not the actual photo)
I had gotten out of a pretty emotionally/mentally/controlling abusive relationship at the time. So needless to say, I had some apprehension putting myself out there, again. The thought of being vulnerable to someone again was scary.
We spent maybe 30 minutes to an hour at the restaurant. The remaining 5 hours of our date was spent talking in the car about anything and everything. By the time we both (begrudgingly) parted ways for the night, we had a breakfast date planned for the next morning, and it felt like I had known this man for years. It was the first time in a long time that I was able to fully relax around a guy, especially on a first date. So it wasn't anything specifically that was said or done, it was just the way we opened up so easily to each other, even about insecurities, past relationships, etc. He just made me feel...comfortable.
We're coming up on our one year anniversary here in a few days. The road hasn't been completely smooth, as the first healthy relationship after an abusive one can be pretty rough when you've experienced/learned nothing but toxic coping mechanisms and have to unlearn them. But man, I think this is the first time I can truly say I know what it feels like to be loved by a partner fully.
#9
Image source: Scorponok_rules, Vija Rindo Pratama/Pexels (not the actual photo)
It just felt right being together after about 5 minutes into the date.
It's been 13 years since that first date and the feeling still hasn't changed.
#10
Image source: romeosgal214, Viktoria Slowikowska/Pexels (not the actual photo)
He gave me flowers that he picked and tied a bow around, then took my hand to lead me into the restaurant. We’ll be married 14 years in October.
#11
Image source: azninvasion2000, Jep Gambardella/Pexels (not the actual photo)
She insisted on paying for dinner, then busted out a mini travel backgammon set from her purse and asked if I knew how to play.
#12
Image source: brsb5, Breakingpic/Pexels (not the actual photo)
1985, he liked rock music, I like country music. He borrows The Judds cassette from his brother and has it playing when we get in the car. Been married 36 years.
#13
Image source: Available-Line-4136, Tima Miroshnichenko/Pexels (not the actual photo)
She yelled at some teenagers to be quiet in the movie theater. We are married now.
#14
Image source: HatefulTwon, Edward Eyer/Pexels (not the actual photo)
This girl I was dating a few years ago did an impression of a T Rex on our third date, and she went ALL OUT. Little arms at her chest, big dino steps, full effort roar. I knew I'd marry her from that moment.
We got married last summer. We have a little dinosaur on the way this October.
#15
Image source: anon, Min An/Pexels (not the actual photo)
I met a guy on match.com. We talked for a bit and finally met in person. Honestly, I was kind of "meh" on him. He seemed a bit standoffish. We went out to dinner a restaurant I liked, had a great meal and then he asked if I wanted to go for ice cream. I was like "sure" so we went to a nearby ice cream shop, had some ice cream and talked some more. I was still on the fence about him.
So, we finished our ice cream, it was after 10pm and we were getting ready to head out. He looked at me and said, "I had a really great time tonight and want to see you again. How does 7pm next Saturday sound? I can pick the restaurant this time."
I did admire his directness and figured "Why not?" So, I said yes, we went out the following Saturday and he was like a different person - much more relaxed, chatty and open. I later found out he was a *nervous wreck* on our first date because he really liked me and didn't want to "mess it up" (his words!).
Well, he didn't mess it up. We've been married almost 20 years now and have two great kids. :-).
#16
Image source: eye_snap, Ron Lach/Pexels (not the actual photo)
We were at his home, alone for the first time. His friends called, he was on the phone for a second, then when he hung up he said "I am so sorry, I gotta go, my friends have been drinking and they dont want to drive, I'll go pick them up, I'll drop you off on the way."
We ve been married 10 years now and that was the moment I fell in love.
It might seem silly, but I was really impressed how he didn't hesitate, like of course his friends could count on him, even when he had the house to himself with his date, he was still thinking "my friends need help". And he is mature and responsible, he worried that they might try to drive while drunk.
I thought this is a reliable man who has his priorities right.
And he has proven himself to be exactly that over the years we've been together.
#17
Image source: ariesgeminipisces, Matthias Cooper/Pexels (not the actual photo)
He just made me laugh the kind of laugh where I throw my head back and laugh from my heart and belly. He still makes me laugh like this.
#18
Image source: DianaPrince2020, Tobi/Pexels (not the actual photo)
As we were driving to dinner a car swerved into our lane causing him to have to brake hard, he automatically put his arm out over me. It was something my mother always did. To me, it symbolized an unthinking care and thoughtfulness.
We will be married thirty years this month and he is truly thoughtful, empathetic, and caring. I told him he is simply a good man. That is high praise to me. Nothing better than a genuinely good person.
#19
Image source: kindahipster, cottonbro studio/Pexels (not the actual photo)
I went on a first date with my now husband at 18. I'd been on dates before but they (being teenager dates) were always pretty awkward, even if we liked each other and we're doing fun things.
The thing about this date was that, it was kind of weird and seemed like it shouldn't go well. First, I was waiting outside for him to pick me up. He asked if he should introduce himself to my family, and I said no because I had a bad family situation and it wouldn't be beneficial for anyone to do that, but I thanked him for asking. He immediately was fine and we drove to the restaurant.
I complimented the stickers on his console, they were for some rock bands and looked cool. He thanked me and said normally people just compliment the car because it was a Corvette and didn't like his stickers. I had no idea what kind of car it was and apologized but he said it was fine, the car was a handmedown from his brother so he didn't care about it and liked that I liked them.
We get to the restaurant and I warn him, embarrassed, that I'm a messy eater. I don't mean to be, in fact I try very hard to be careful, but I've always a bit of a disconnect between my hands and mouth, and always end up with a bit of sauce on my shirt (I didn't know it then, but I know now I have ADHD). He said that was cool and wasn't judgy at all, even when my tomato fell off my BLT into my lap, and we laughed about it together.
After a bit of small talk, he said he likes to be direct and of it's ok if he asks more personal questions about what we want out of life and stuff. I was thrilled, I hate the "waiting several dates before talking about serious stuff" thing because it always felt like a waste of time. We talked about religion (none for both) marriage (maybe but not for a while), kids (no for both), life goals (both to find nice, relaxing jobs to make enough to focus on hobbies and some travel), politics (left leaning). We weren't the same in every way though, when it came to hobbies I like reading, movies and crafting. He liked video games, d&d and coding. We both were very interested in the others hobbies as well. I felt really at ease with him, even when I had answers he didn't quite agree with, he was very interested in what I had to say.
When we leave, we had planned to hang out at a park after but it was raining. As we were walking to the car, he paused and said "Ive never kissed someone in rain before". I was blown away at how romantic it felt and we had a perfect, sweet kiss.
We hang out in the car a bit longer before he dropped me back at home. He thanked me for a wonderful time and kissed me again (again sweet and not asking for more). I was giddy, once inside I immediately called my best friend to gush about it. She thought the date sounded weird, but was happy for me. I then said I really wanted to text him *right then* because I liked him so much. My friend was horrified, and said I couldn't text until at least tomorrow and to preferably wait for him, or else I would seem desperate. Literally not 5 minutes late while still talking to her, I get a text from him saying "I think I'm supposed to wait longer before texting, but I couldn't help it, I just wanted to tell you again what a good time I had".
It all felt so magical, not because it looked like something in a movie, but because it looked exactly how I would write a romance for me. 10 years later, we are still incredibly happy together.
#20
Image source: throwaway47138, Lina Kivaka/Pexels (not the actual photo)
The first time my (now ex-, but we were married for 16 years and have kids together and I don't regret it) wife visited my apartment, my one cat that was notorious for disappearing when anybody came over (even the pet sitter who he knew well and liked) promptly jumped on her lap and started purring at her. She had no i idea what to do with cats at the time and said so, but just went with it and they became friends right away. If he thought she was a keeper, who was I to argue with him.
#21
Image source: swordofBarsoom, Stanley Morales/Pexels (not the actual photo)
When we had our first date, it was actually our first time seeing each other in person.
He met me outside of my office right when my shift ended… and literally ran across the street to me with the biggest, brightest smile. He took me in his arms and hugged me so hard that my feet dangled in midair, and in the sweetest and most excited voice he said:
“It’s so nice to finally meet you.”
Ten seconds in and I was COOKED. I loved that he never tried to play it cool or aloof. He never hid that he was happy to see me.
He literally swept me off my feet.
That was three years ago, we’re getting married in October.
#22
Image source: GoramReaver, Lukas/Pexels (not the actual photo)
On our first date, some of her ice cream dripped onto her sleeve. Nonchalantly wiping it up, she told herself, “can’t take me anywhere…”
I smiled. She’s been my wife for 7 years now.
#23
Image source: Any_Assumption_2023, Katerina Holmes/Pexels (not the actual photo)
He quoted my favorite poet, TS Elliot, at the dinner table on out first date. I finished the quote. He stared at me across the table for a stunned moment. I swear that was the very moment we fell in love with each other.
#24
Image source: ginger_ryn, Dziana Hasanbekava/Pexels (not the actual photo)
First date with my partner
i told him i had trauma and cptsd and adhd etc. he asked “what does that mean for you?”
instead of judging, asking probing questions, or ignoring it completely, this man asked me how this impacts my life, in an effort to genuinely understand me and my mind
our 6th anniversary is next month.
#25
Image source: Mushrooming247, Askar Abayev/Pexels (not the actual photo)
He said he couldn’t hang out the next night because he was making dinner for his grandma and mom and aunt.
Definitely a green flag. We have been married for 20 years.DE
Written by
Demilked Editorial
SaaS Review Specialist · Demilked
With 5+ years in the creator, entertainment, and publishing spaces, Demilked shortlists, reviews, and ranks leading tools that actually make your life easier.