Your dating past is always a tricky conversational topic to broach with a lady you’re going out with, but it’s even more problematic when you’re older and you have a long and extensive dating past to discuss.
Here are a few important points to keep in mind to make this conversation go as smoothly as possible.
1. Give a summary and that’s it.
You’re under no obligation to tell your new lady every single thing about your past. This is obviously true when you’re on a first date with a woman, but it remains valid even after you have been seriously dating someone for a long time.
Tell your woman the greatest hits of your dating life and anything important that will come up as a relevant element of your relationship (like if you had a wife and have kids and grand kids), but beyond that, you are under no obligation to share all.
As a side note, the same is true in reverse. You don’t need to know everything about your new woman’s dating life, and you shouldn’t push for anything more than the Cliff Notes version of how she got where she now stands, which is with you, after all.
2. Only cover the biggest points on dates.
It’s natural to talk a little bit about whether you just got out of another relationship or whether you’ve been married in the past (and how many times), but don’t feel like you need to keep that conversation going after it crops up.
The first couple of times you go out with a woman you should focus on seeing if you like and enjoy each other and that’s it.
Share the above-mentioned Cliff Notes review of your dating history for when you start thinking about committing to each other in some serious way.
“If you set the tone, talking about your
dating past will be a productive experience.”
3. What you’ve learned and what you now seek.
Your past dating life is only important insofar as it made you the man you are today. So instead of fixating on the past and getting lost in either nostalgia or bitterness, move quickly from discussing the details of your dating past into talking about how that past has impacted your growth as a man and as a relationship partner.
Women want to know what your past dating life is like because they are curious about who you are and how you became that man. They don’t really care that much about 30-year-old gossip.
Having this more expansive conversation is also a good way to make sure the two of you are on the same page and understand each other’s current dating expectations.
4. Be brief.
Instead of focusing on the past, you should focus on the here and now. Women are perceptive and they will only continue a conversation about your dating past if you keep rambling about it.
If you make it very clear what happened in your dating past, how you felt about it and how it changed you, then your woman will likely feel satisfied.
Likewise, keep your questions similarly brief and refrain from asking more follow-up questions than you really care about. Keep the conversation moving so she doesn’t keep talking in circles.
If you set the tone and the pace of the conversation and stick to it, talking about your dating past will be a productive, shared experience instead of a painful chore.