Arielle and Bailey Spill the Tea On Their First Kisses and Heartbreaks

No topic is off-limits in our 20/30-Something series.

We've covered budgetingdating, and relationship advice, and now we're tackling the most personal topic of all–our "firsts."

Arielle and Bailey are spilling the tea on milestone moments like their first kisses and the painful memories of their first heartbreaks. Spoiler alert: it gets juicy. Prepare yourself for majorly revealing details in our candid 20/30-Something storytime below.

20-Something Storytime: Bailey On...

Her First Kiss: I was a late bloomer–my friends were all kissing boys in 7th grade and I was so nervous about it. Then, when I was a freshman in high school, I was talking to a boy who was older. I was thought to myself “I need to kiss someone before it comes to me having to kiss him, because that would be so weird!” I went to a party one night and my best friend got two of her guy friends to kiss me! So my first kiss was two kisses in one night. I’m still friends with them to this day and we laugh about it all the time.

Her First Relationship: In my first real relationship, I "forced" this boy I was obsessed with to date me. We grew up together and I always thought he was cute. He wanted nothing to do with me for two years and I was like “one day you’re going to date me” and eventually he did! We dated for 8 months and then he went to college, so it ended. It was very amicable.

Her First Heartbreak: To be completely honest, in all of my serious relationships, I’ve always been the one to break up because I fall out of love kind of easily. I have no real reason why, but I don’t want to waste anyone's time if I’m not in it 100%. I’ll never forget the first time that I got my heartbroken. I was seeing a guy who was older and he came to my house and said “I can’t see you anymore, you’re too young and my parents don’t approve and it just doesn’t make sense.” I have never felt like that before–your heart gets punched, it’s the worst feeling in the entire world. My advice is to feel what you feel and go through the emotions because if you try to ignore it, it may ruin relationships later. Go through the motions and eventually, time heals all wounds. And you’ll find someone better!

30-Something Storytime: Arielle On...

Her First Kiss: My first kiss was at camp. I was 14, we went behind a cabin, and he kissed me!

Her First Relationship: My first real relationship was my junior and senior year of high school. He was a really cute guy who was really cool and popular (and I was not at all). He went to a different school. One of the girls from the cool group at my school invited me to a party one night, and she was like “oh that’s so-and-so and he’s really cool.” In my head, I was like “there’s not a chance,” but somehow we talked for a few minutes, and then we started IMing. He was not really interested in me but he was talking to me a lot. Finally, at the end of junior year, we started dating and we were together for a year. I lost my virginity to him and went to prom with him. When I went to college, I just wanted to be single and I wanted to move on, so I broke up with him. It was not an amicable breakup and it was very rough.

Her First Heartbreak: The first time that I was heartbroken was a year before I met Brandon. It was devastating, like the worst feeling. I can’t even explain what it felt like. For me, the best piece of advice was to grieve the end of the relationship and just get back out there and keep yourself occupied. Once you find someone new (who you’re in love with), you’ll be happy you moved on.

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Interviews have been edited for length and clarity.