On the brighter side, try to do things that seem more casual. Instead of going out to dinner, go out to lunch or meet up for coffee. If this mini-first date goes well, you can make evening plans that involve a romantic restaurant or event. Doing a mini-first date will also let you end the date quickly and move on if it is not going well.
Other than dinner, you can arrange a museum tour, get tickets to a sporting event, or go to a local comedy club or live show. You can go to a wine tasting, or if he is an outdoor type, you can plan a hike or picnic in the park. If you have no solid ideas, don't be afraid to call and find out what kinds of things he likes.
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