Dear Wendy: “She Hasn’t Paid For A Single Date Yet”

I met someone online and we’ve gone out five times. We’ve gone to two nice dinners, brunch, a movie, a night of bar hopping and our first date, which was drinks that lasted until 2 a.m. Things are going pretty well. So far, I’ve paid for everything we’ve done. She hasn’t made so much as a reach for a check. Like Seinfeld once said, “it’s nice to get a reach.” I’m a single father and I have a lot of expenses to deal with. It’s not like I can’t afford her, but I don’t want to feel taken advantage of either. She’s got a good job, so I’m pretty sure she’s not struggling. How do I let her know I don’t like paying all the time, but I’m more then happy paying most of the time? — No One’s Chump

Dude, not even a reach? Not even a little one? I hate to say it, but if, after five dates, the woman hasn’t even so much as made an attempt for her wallet, she probably falls into the camp of women who believe a man should plan and pay for everything. If that’s a dealbreaker for you — if you think that says something about her character and values that doesn’t appeal to you — it’s better to find out for sure right away whether that’s the kind of woman she is. The easiest way to do that is to come right out and tell her you’re really enjoying her company and you’re happy to pay for most of your dates, but you’d appreciate it if she planned and took care of the occasional date as well. If she balks at this idea, you’d be ahead to run in the other direction. If she’s this self-absorbed and thoughtless now, imagine how she’ll be in the long-term.

If the aggressive approach doesn’t work for you, you could always give it a few more (cheap) dates to see if she ponies up. My guess is she won’t though. She’s already had plenty of opportunities — like offering to get drinks at one of the stops on your night of bar-hopping or covering the movie tickets — to make the token gesture of paying without spending too much money. You could give it another couple weeks and see if she invites you over for a home-cooked meal, something women who are philosophically opposed to paying for dates often do as a goodwill gesture. But maybe that wouldn’t be enough for you anyway. Or maybe it would be too little, too late (I wouldn’t blame you). You could also invite her out one more time and suggest going dutch and see what her reaction is. If it were me, and she didn’t say something along the lines of, “Oh, let me get this one — it’s my turn,” I’d take that as my cue to find another woman — one who doesn’t have a princess complex.

I’m 21, smart and pretty. I just met a seemingly perfect guy in a new class I’m taking who seemed interesting from the moment I saw him: open, friendly, hot. We got to flirting and exchanged numbers. I’m always the first one to text him, but he responds readily and in a flirty way, calling me “darling” and all. Then he invited me over; I said yes, he drove to my place, opened the car door in front of me, took my jacket — I felt like I was with a grown-up man for once. He showed me around the house. I met his parents. Everything was going great and we made out with a movie on the background. I kept my pants on, but things were getting hot and he was totally into it. At midnight, he drove me home and said he would call me the next day. The next day, no call. Day after, nothing. Week later, in class, he completely ignored me. I tried to flirt — nothing. I texted him a couple times over the week and he hasn’t responded to anything more personal than “hey sexy, how you doing?” I don’t understand what could ruin it so bad after the Perfect First Date. I guess he isn’t that into me, but if he just wanted to “hit it and quit it,” why stop before sex? I really like him. He’s gorgeous, smart and a “can do” type of guy. Everything was great and I have no idea what made it change. I want him to be mine! But I don’t understand why is he doing this, don’t know what to do and it’s driving me crazy. — Confused

I don’t know whether to be more concerned for you that you consider going to some guy’s parents’ place and making out with a movie on in the background as “The Perfect Date” or that you can’t figure out why this guy no longer seems interested in you. He thought you were going to be an easy lay! You aggressively sent him flirty texts, jumped at the chance to go over to his place, and when you didn’t give it up right away, he didn’t see the point in wasting any more time on you. That’s because he really was never interested in you as a person — he was just looking for a sure thing, which he (wrongly) assumed you were. If he’d been interested in anything more than sex with you, he’d have actually made a real date, not just invited you over for a booty call. If he’s as gorgeous as you say he is, he probably has girls like you fawning all over him. In his mind, you’re a dime a dozen and he doesn’t need to waste more than one evening trying to get in your pants. If you won’t give it up right away, there’s probably a line of other girls who will. He’s moved on and you should too.

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

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