Second Time Around?

It’s been three years since my breakup and I’m single and dating. I ran into my Ex in a bar and now he’s leaving me messages asking me to get together because he’d like to try again. I’ll always have a soft spot for him… should I consider a reconciliation?

Sinatra sang that love is lovelier the second time around, but the lyrics leave out the drama that led to the first breakup. Only you can determine if you’re in a place where you can learn from the past, leave the past behind and move forward in a positive and healthy way with your Ex. Resolution can happen and people can change if they learned from their mistakes. If you both have achieved that enlightened education, then having a Round Two isn’t out of the realm.

I matched with a guy (he seemed familiar at the time I swiped right but I couldn’t place him) and we matched. We actually had a date ten years ago and nothing came from it. He seems not to remember… should I tell him before the day of our “first” date?

Timing is everything, and maybe ten years ago you both weren’t ready for each other. Jumping into the “First Date Time Machine” could be a lot of fun and in the very least interesting. I would tell him on the date so you can see his reaction. Have fun!

My wife and I had a “quickie” wedding as soon as marriage for us became legalized. We regret not having a “real” ceremony and party. Do you think we look stupid doing it now (and we also now have two kids!).

Of course not! If you and your wife want to have a vow renewal with all the fixings you should go for it! It will be even more special because your children get to be a part of it and your friends and family will surely be on board. Enjoy every moment of the planning (it can be stressful but definitely fun) and making memories on your special day!