I recently moved back to my very small hometown after 30 years and reunited with an old girlfriend. My family is totally against the relationship because of my friend's past life as a so called 'party girl.' I was told that she dated one of my family members, but I have not asked her about it because I am not sure if this is any of my business. Where should we draw the line in terms of where a lover's past should inform how we go forward with our future? Would I need to, say, disclose if I had once been in a swinger's club?

My dear love muffin! Sure, it would be nice for your family to be supportive of the person you may choose to spend the rest of your life with, but it certainly isn’t necessary.

Often times people in our hometowns tend to think negatively of those who choose to do things outside of what everybody else is doing. Anything different from the norm is labeled negatively or judged—- i.e the ‘party girl’ rep your lady friend has.  I’d like to point out that being a former ‘party girl’ isn’t necessarily a bad thing. It could simply mean that she likes to enjoy life (and might even have a few more womanly tricks up her sleeve.) 

However, I do feel that the issue of her dating one of your family members should be addressed — if only to provide you with the knowledge to know how to navigate a potentially awkward encounter. Meaning you wouldn’t want to be at the family reunion with her in tow and unknowingly run into the family member she was involved with.

You both need to be in a place where you’re comfortable with one another. Take it slow and get to know each other all over again. You’d be surprised to see how much a person can change in 30 years. 

And yes, you should definitely mention if you once belonged to a swinger’s club. You never know, she might be into that! Plus, that’s not something that you would want her to find out from someone else.

At the end of the day, when you truly love someone, you don’t judge them by their past. You leave it there, happy that their future is with you.

Love,

B. Scott

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