The Gentleman's Guide to Shopping for a Lady

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Valentine's Day is just around the corner, and you may be wondering what to give a special lady in your life. Here are ten guidelines for success when selecting a thoughtful gift for her.

1. Proceed boldly.

Shopping for a lady takes thought, resourcefulness, and skill; proceed boldly and with confidence. A gentleman in pursuit of a suitable gift for a woman in his life—whether his wife, girlfriend, mother, other relative, or a friend—is always a pleasant sight to behold.

2. Always purchase your gift at a store where you can get a full refund.

Purchasing gifts at stores with excellent refund policies is a wise decision when shopping for a lady, as it may turn out that your gift doesn’t fit her or is not to her liking, and it is possible that the lady may not be able to find a suitable item in the store to exchange for it. Be sure to make her feel at ease that she is most welcome to choose another selection with no guilt attached. You can go shopping together to find another gift, or she can surprise you with her selection if she chooses the replacement on her own.

Some stores mark items down from artificially high retail prices, making them appear to be better deals than they are. Fine jewelry is an area where men—and women—can be easily taken advantage of with “sales,” even in our smartphone age. When shopping for jewelry, do your homework to find a reputable retailer, and try to avoid making an impulse purchase.

3.  Be as generous as your budget allows and is appropriate for the stage of your relationship.

If a lady receives an overly expensive gift from a gentleman to whom she is not married or engaged, it can place her under a feeling of unnecessary obligation. Be mindful of your budget and show the lady that you know how to handle your finances responsibly. Don’t be stingy either. There is a fine line between being frugal and being a cheapskate.

4. Be strategic when selecting a certain size of clothing.

This is a real land mine for gentlemen when buying clothing for a lady. What if you select a size that is too small? The lady may be embarrassed that it doesn’t fit her. What if you select a size that is too large? This may also send a displeasing message. One solution is to avoid buying any kind of clothing for a lady, but this limits your shopping choices. Thankfully, there are solutions to this dilemma.

The lady may routinely do her shopping with a certain salesperson at her favorite store (it is wise to build such relationships, as smart salespeople wisely keep their clients informed about upcoming sales and new discounts). You can ask this salesperson what size the lady normally wears. If the clothing item doesn’t fit, you can place full responsibility for the size selection on the salesperson, freeing yourself from any unintended implications on your part. The lady may also have online shopping wish lists with her favorite merchants from which you can shop as well.

5. Present your gift with care.

There is really no excuse for presenting a lady with a sloppily wrapped gift, unless it is unusually shaped (when giving a large item that is difficult to wrap, place a big bow on it or something else that is festive). If you wrap the present yourself, the lady will likely find your effort most endearing, regardless of the outcome. If you are not proficient at wrapping presents or prefer not to do so, stores usually have someone working there who will be happy to help you (often free of charge) to make a lovely presentation with paper, ribbon, etc. provided by the establishment. Consider surprising her when presenting your gift (in a way that is not embarrassing, of course!), adding even more merriment to the occasion.

6. The thought does count.

A gentleman with sufficient means can dash into any store and buy an expensive present in minutes. Yet, a true lady’s affections cannot be purchased. You will look far and wide before you find a woman who will not be extremely pleased when a gentleman puts considerable thought into his gift selection for her.

7. Giving a gift does not require spending money.

It may occur that a gentleman goes shopping and is unable, for a variety of reasons, to find anything suitable for the lady. He may thoughtfully and wisely choose to give her something that does not involve money being spent. There are so many possibilities when it comes to giving the gift of your time. Plan a walk together in a picturesque area; go star-gazing at a nearby beach; window shop along a trendy street; watch a movie together at home; offer to wash her car or tend her garden; accompany her on a visit to an older relative or friend who is lonely. Check out the free activities in your area and see how many you can do together in one day. Be creative.

8. Ask advice from a friend or relative of the lady.

Gifts send a message, and it might not be the one you want to send. Chocolates: “Doesn’t he know I’m on a keto diet?” Workout clothes: “Does he think I need to lose weight?” Sailing lessons: “Doesn’t he know I don’t like watersports?” It’s enough to make any man apprehensive. When in doubt, ask a close friend or relative of the lady what she would enjoy receiving.

9. If you can’t afford a certain gift for a lady but sincerely wish you could get it for her, say so.

This means more to women than you might realize. The lady will appreciate that you have contemplated getting her such a gift, and she will likely inform you that there is only one present she really wants—and that is the gift of your delightful company.

10. Enjoy the process.

When you give a gift, you are giving of yourself. Presenting someone with a gift you have selected with thought, care, and the sacrifice of your time and money is an art as well as a skill. Don’t rush into taking the easy way out and select the same present again and again just because you know it was a good choice on one particular occasion. Think outside of the box, take some chances, and enjoy the journey of showing your regard for the lady in your life through the beautiful act of gift-giving.


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