Dear Wendy: “Is It OK To Call Guys For A Second Date?”

I’m a woman on the cusp of her 30th birthday and have enjoyed my single status for over a year now, but am looking for a relationship again (I had three serious ones throughout my twenties). About a year ago, I joined an online dating site, and have had no shortage of first-dates, but very few second dates. Granted, I don’t always want a second date with every guy I go out with, but I’m baffled when my date seems to show genuine interest and then I never hear from him again. So my first question is this: do women really have something to lose if we go ahead and call after a date to take a man up on his offer? Several friends are insistent that calling after the first date makes a woman look desperate, end of story. I am not sure how many more blows I can take in this department — there’s always the nagging question of, “What if I had just called?” I’m also wondering if there’s some “secret” I’ve been oblivious to in the past year that will magically make me more successful in the dating world. I believe I’m a “catch” and I know all the first-date don’ts: don’t drink too much, don’t talk about your ex, don’t sleep with him or come on too strong, etc. Is there something else I should be (or not be) doing? — Tired of Being Single

Here’s one thing I know as a truth about guys: if they’re interested in seeing you for a second date, they’re going to ask you … especially if you’ve shown even a hint of interest in seeing them again. If you’ve gone out with a guy once and he wants to see you again, nothing will stand in his way of asking you for a second date — not fear of rejection, not a “cold,” not a busy week at work, not rain, sleet, snow or a city-wide blackout. He’s going to call. Does that mean that every guy who doesn’t call wouldn’t go out with you if you asked? No, not necessarily. Flattery, guilt, and a wide open schedule with a dash of boredom could all motivate a guy who wasn’t initially interested in pursuing a second date to give you another chance if you took the reins and asked him out. That being said, if you’re already saying you aren’t sure “how many more blows you can take in this department,” I wouldn’t risk possible rejection by asking for a second date.

After a year of what you seem to consider failed dating, your confidence is shaky and you’d be better off working on getting it back rather than throwing yourself into possible ego-busting situations. I speak here from experience. There’s nothing worse than already feeling like a loser in love and then getting rejected for a second date by a guy you’re only “eh” about anyway. I suspect you feel like you’re in a bit of a race to find someone. The whole “on the cusp of your 30th birthday” thing makes me think you’re hearing a ticking clock you’re trying to beat. And I get it; I do. The older we get, the pool of eligible bachelors to choose from gets smaller. But the “secret” you’re looking for in attracting a mate isn’t about numbers or silly dating rules, it’s about having a positive attitude. When you radiate positive energy, it’s magnetic; it draws people in. So, quit thinking in terms of “don’ts” (first date “don’ts,” you “don’t” get many second dates, you’re almost 30 and “don’t” have a relationship, you “don’t” know what you’re doing wrong), and think in terms of “dos.” Focus your attention on what you love and fill your life with more of those things. It sounds simple because it is. A happy person who loves her life is attractive. Learn how to love your life without a man in it and you’ll be amazed how much more successful you’ll be in finding one.

My best friend and I are so close, we’re like sisters. We’ve been friends for years and have done just about everything together — we even have small matching tattoos. This past weekend she and her only sister and I were talking about her upcoming wedding. My friend had already asked me to be her maid-of-honor but didn’t tell her sister about it. When we began discussing the dresses, her sister became irate at the fact that she isn’t the maid-of-honor. I felt really bad because they are sisters and I could never break that bond; however, part of me was a little upset when my friend’s sister said it was her right to be the maid-of-honor. Should I step to the side and let her have that honor or should I stand my ground as the best friend? — Honorable

I admire your desire to keep the peace between the sisters, but the truth is it isn’t your call who’s maid-of-honor in your friend’s wedding; it’s hers. Sure, you have every right to decline the offer, but just because you do doesn’t mean your friend will automatically choose her sister to replace you. Judging from her sister’s immature and selfish reaction to the news, your friend probably had good reason not to ask her to be maid-of-honor. She chose the person who was best for the “job,” but if you’re feeling guilty or awkward about taking the position, you can always pull your friend aside and privately ask her if it would be easier on her if you stepped down. Let her know how honored you are to be asked to be her maid-of-honor but you don’t need a special title to know how much you mean to her. It’s a gracious move on your part and will show your friend who really has her back. Just make sure you’re OK with whatever answer she gives you. Your friend doesn’t need two people hurt by her wedding party decisions.

*Do you have a relationship/dating question I can help with? Send me your letters at dearwendy@thefrisky.com.

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