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How many times have we reflected on missed opportunities and foolish mistakes we made during our dating years and thought, “If I only knew then what I know now.” The beauty of starting over again after all these years is that now you do know all the things you didn’t know when you were young, so this time around should be smooth sailing by comparison.
Still, it’s not easy to dust off the old charm and bring the confidence you need to impress a new lady who’s been around the block a time or two. You might think that by now you should be immune to first-date jitters, but you will be a lot more relaxed if you know you have a great date planned that she will love.
This may be the first time your date has been with a new man in many years. Even if she’s an active dater, she has more concerns on her mind now than she did as a carefree teenager or young adult. She probably has grown children and a long history of fidelity to one man.
It may take her a little time to get comfortable in the company of a new fella, to be seen in public with him, and to experience his touch, even if it’s just holding hands. You want to put her in the most nonthreatening situation you can.
A daytime stroll by the lake or through the park will create less predate tension for her than an evening on the town. She won’t have to worry (so much) about what to wear, how her hair looks, or how women are doing their makeup these days.
It’s low pressure for her without a lot of the preconceived romantic expectations to worry about that go along with dinner and dancing or a movie and drinks.
A leisurely walk with a stop at a quaint uptown diner, and maybe a swing by the Dairy Queen on the way home, might be just the way to win her heart with a fun afternoon of conversation, fresh air, sunshine and trust-building activities.
You might also try a museum, art exhibit, free concert in the park, or any daytime activity. Surprise her with a short smack on the lips and some nice words when you leave her at her door, too.
“You want to show her you
respect her and care for her.”
This could be a daytime or evening date. Find a bookstore in a nice mall that has a coffee shop inside. There are many subjects for conversation all around you, and you can learn about each other by the things you each like to read, whether they are magazines, newspapers or books. You can also share a hot or cold beverage and some good conversation as you plan your next adventure for the afternoon or evening.
From there, it’s a short walk to a variety of high-end, family, ethnic, or fast food restaurants. The movie theater, people watching, window shopping, or just walking out into the cool night air can be an amazing experience for you and your lovely lady.
You can let fate or her interests determine the course of the date. If things don’t go well, either one of you can end it at any time without an awkward or lame excuse.
It’s very possible that you will meet a high-maintenance girl with more formal expectations for a date. When you suggest Chipotle, she might just tell you that if you want to date a lady like her, you’re going to have to take her to a five-star restaurant with music and drinks. Or you might be a man of means who wants to impress her and court her in style.
If she’s ready for a formal date, dress to kill. Be sure to tell her how beautiful she looks. She may not have heard it for a long time, and she may have stopped feeling attractive.
She took a long time to get ready for you, so notice some of the little things — her hair, her nails, her shoes, her broach — and express the appreciation you feel to be in the company of a lovely lady.
Bring a nice bouquet when you pick her up, and let her put them in a vase at home so she doesn’t have to carry flowers around all night. Pull out a single flower for her to take along, and ask the maitre d’ for a vase when you get your table.
Start with wine and an appetizer before you even look at the dinner menu. Talk until she laughs and begins to relax. If she is having difficulty deciding between two entree items later on, tell her to order one, and you order the other one for yourself. Then you can share.
Sharing bites of a meal can be very romantic, and it adds a personal and intimate feeling to the experience. A brandy Alexander, grasshopper or other dessert drink afterwards would be a nice finishing touch.
You’re not kids, so you don’t have to wait forever to get romantic. But first-date romance should be just enough to light the fire. A warm embrace and magical kiss on her doorstep might be the perfect ending. You have the intuition and skills now to know if she’s in the mood for it.
No, you’re not going to jump her bones on the first date. You want to show her you respect her and care for her. But you also want her to know she can still turn a man on and that you’ll be able to fulfill all of her needs as soon as she’s ready.