The Question: I have a second date with a special girl. I live in the Cleveland Ohio area. I found a place we can go to see x-mas lights on a horse-drawn wagon. She has a daughter and I’m thinking she is ready to settle down.  I really like her and I’m ready to settle down. Do you think that the horse drawn wagon is a good idea and not too pushy or romantic?

The Answer:

The horse drawn carriage ride definitely sounds romantic and also very thoughtful. Everyone goes to dinner at some fancy place on their first dates – that’s not special. She’ll appreciate that you actually came up with something creative and romantic.

If you want to stand out from the crowd, always strive to be yourself, to be different… Don’t go on the same dates everyone else goes on, and don’t copy what everyone else does. Do something exciting and memorable, and most importantly – have fun.

Fun and happiness is extremely infections… people just can’t get enough.

One caveat… if she seems at all uncomfortable around you, then it may be best to take her to a more public place place like a restaurant. That way she won’t spend the evening with her guard up and the two of you should have a lot more fun. That’s usually more of a first date issue, but still keep it in mind.

In the end, you two will have to decide together. Tell her what you’re planning and let her choose what she’s most comfortable with. Better yet, brainstorm some ideas together, and come up with fun ideas for future dates. That way you’re way more likely to reach third date and beyond.

A word of caution on the topic of settling down… you’re not there yet. Don’t rush it. If you’re too focused on the end goal of "setting down" you could sabotage the relationship before it takes off by being too pushy or needy. When the time is right and you’re more comfortable around each other (you’ll know when that is…) – talk openly about how you both honestly feel about settling down. Make sure that you have that conversation in a neutral, no pressure environment and be prepared to listen to what the other person has to say.

Take this one day and one date at a time. Enjoy your time with her now and see how your relationship grows and evolves.

You’re definitely on the right track… keep it creative and exciting and fun.

For some fun and really unique date ideas, check out our review of Michael Webb’s excellent book 300 Creative Dates.