Dating a woman (28) who’s never had a relationship before - thoughts?
Hey everyone,
I’ve been following CCW for a few years now, and it’s definitely made me a lot more successful with both hookups and relationships. But I haven’t really come across much on this specific topic: dating women in their late 20s who have never actually been in a relationship before.
For context, I’ve been seeing a 28 y/o latina in spain for about 7–8 weeks and things are going pretty good so far:
- Fun dates + trips (even did a 3–4 day weekend trip together)
- She initiates 100%, good s*x multiple times per day..
- No drama at all, but it's still very early.
- She cooks/cleans when she’s over, helps economically, and is genuinely invested
- Recently told me she’s falling in love + brought up exclusivity
I like her a lot, but I’m not in love nor completely sure yet. What’s on my mind is the fact that, despite being 28 and sexually active since 22, she’s never had a real relationship. From what she’s told me, she’s always dated with the intention of a relationship, but her experiences have not the best and been hurt a couple of times.. it’s usually ended up being 3–6 month flings (men not wanting commitment) or situations she broke off because of incompatibility (like substance use, which she’s totally against).
I’m 32 myself and have had 3 relationships over the years, so I’m a bit unsure how to see this. Is it something I should treat as a potential red flag, or is it more understandable given hookup culture here in Spain where people rarely settle before 30?
Posted Sep 8, 2025, 1:59 PM UTC