I got into a discussion with an acquaintance about a never married, childless man marrying a divorced woman or marrying a non divorced woman with higher numbers.
I like this discussion as this is a somewhat realistic scenario. This is relatable to me as a never married, childless man.
Over the years, the majority of my interactions have been with never married, childless women. I have had the occasional interaction with a childless, divorced woman. I think part of the reason that I have had few interactions with childless, divorced women over time is that most women get divorced after they've had children.
You didn't specify the number of children that this hypothetical 30 year old woman has had from previous interactions.
For the purposes of this evaluation, I will consider both women to be childless women.
The divorced woman with only 1 past sexual partner likely married her high school or college sweetheart. If she got divorced at 28-29, she was probably married around 21-24. This is a woman with uncommon attributes for a Millennial generation woman. Considering that she is 30 years old in 2025, she was born in 1994-1995, making her a late Millennial. She would have been uncommon even among 1981-1989 born Millennials. A woman with one sexual partner and one divorce at age 30 in 2025 would be more likely to be an active practitioner of a religion. She showed a lot of sexual restraint during her prime years and she got locked down earlier in life. I have interest in knowing the circumstances surrounding the failure of the marriage.
The never married, 30 year old woman with 5 previous sexual partners seems like a serial monogamist. I doubt that she's had more than 1 short term sexual encounter. She has likely shown some sexual restraint, but less sexual restraint than the previous woman. Her sexual history is likely 5 relationships of 1-4 years in length over a 14-15 year period going back to high school. I could imagine her having 1 high school boyfriend, 2 boyfriends during the 4-5 years immediately after high school (college, trade school, or work during that time), and then 2 boyfriends from ages 22-23 to age 30. She is likely to have a clearly established pattern. I have interest in learning more about what her pattern has been over time. If she went to college, that's likely what ended her high school relationship as she and her high school boyfriend went to separate colleges and decided to end it because of that. One of her college relationships likely ended as a result of her first post-college job. I could imagine at college graduation and she and her then boyfriend probably got jobs in different cities after college. It would be interesting to see why 5 of her relationships failed in the 1-4 year range.
The divorced woman has the baggage of a failed marriage in her history, whereas the never married woman has a clean history with failed marriages. Although, the divorced woman has a divorce to her name (making future divorces more likely), she has less overall baggage from men. She likely has fewer failed, non-sexual dates. She's likely spent less time on dating apps, less time in the social media DMs, and less time at bars.
As a never married man, I found it somewhat off putting when I went on first dates with childless, divorced women. These dates happened circa age 30 for me and the women were also around age 30. I felt put off at the time because her previously married status seemed unrelatable to me. When I look back on those dates, I realize that I was the one with the incorrect thought process. I was focused more on the divorce rather than the bigger picture of the overall damage from past relationships with men. I did think that it would have felt somewhat off if I were to marry these women in the future because they had done the whole marriage thing before and failed at it.
I don't regret my interactions with these roughly 30 year old, childless divorced women 10+ years ago. The two that I can remember were "one date, no sex, no second date" interactions. I could have done things differently. However, I also doubt that my dates with childless divorcees were dates with women with only one sexual partner in life.
I have typically gone on dates with never married women. Going on a date with a 30 year woman who is a serial monogamist with 5 failed relationships of 1-4 years in length seems typical for a lot of men. It is likely that I will have a 1-4 year long relationship with her that fails without marriage and without children if I can get past the initial few dates and get to sex with her.
The 30 year old woman with a divorced likely got one of the relationships past 5 years, and closer to 10. She doesn't have much of a pattern. With her low body count and proper effort on assessing her role in her failed marriage, she might be a better option for a 5+ year long relationship that could result in a marriage and future children together.
