Dear Wendy: “My Boyfriend Brought His Mom To Our First Date”

I have been dating this 44-year-old guy — who still lives with his parents, I might add — since the middle of August. He is kind-hearted and has a good soul. On our first date he asked me to meet him at a mall I’d never been to, and it wasn’t even a halfway point between us. He brought his mother was with him because she needed to go to the mall for some things and she doesn’t drive. Anyway, in the four-and-a-half months I’ve been with this man, I’ve been doing all the driving down to his place because he claims he has a phobia about going to new places. Once I drive there, we go out and do things around where he lives at places he’s familiar with. He gives me gas money once in a while because I’m a single mom and can barely afford all the gas to drive the 20 miles each way to his place. I’ve told him that maybe he needs to speak to someone about his phobia. Also, once I’m at his parents’ place, he wants me to go up to his bedroom. I don’t know what to do other than to give him an ultimatum that I will not come down to his place until he decides to come to mine? — Designated Driver

If in four-and-a-half months, you are the only person in the relationship who has made sacrifices and compromises — or has made the clear majority of them, anyway — and you have reached a point where you feel stretched to your limit and can’t take anymore, you should absolutely give an ultimatum that your boyfriend come to your place or prove that he is seeking professional help to deal with his phobia. If it were me, and my date showed up with his mother in tow the first time we hung out, there would never have been a second date, but lucky for your boyfriend, you are a more flexible person than I am. The fact that you’ve been putting up with his nonsense for this long means you’re either an incredibly understanding person or don’t think you’re worth more of an effort. If it’s the former, it’s OK to ask for more compromise; if it’s the latter, it’s time for you to do some soul-searching and ask yourself if this is really the best you can do. If you think it is, maybe you could benefit from a little professional help, too.

My boyfriend and I have been together for almost a year and a half. Our relationship has been kind and loving and we have an incredible connection. However, recently we each returned to our respective hometowns for the holidays in different regions of the country, and something troubling happened. I attended a neighborhood party at a male high school friend’s parent’s house on the night of the big snow storm, and between the cocktails and the snow, opted to spend the night rather than try to make it back across town. One of my best female high school friends was with me as well. The three of us have known each other forever and we all piled in one bed to sleep, and I never gave it a second thought; I mean, we used to do this every other weekend in high school and every break during college when we all used to hang out … It’s a strictly platonic dynamic between all of us.

When I spoke to my boyfriend the next day, I relayed the night’s events, and he expressed that it made him uncomfortable that I slept in a bed with another male, regardless of the circumstances. I apologized and was completely understanding, and told him I would crash on couches if something like this ever happened again. I asked him if there was anything else he wanted to get off his chest, but he said no, he was satisfied and that it was no longer bothering him.

The following night, he attended a bar crawl with his college buddies, and I received a slew of nasty texts, including one threatening to “sleep in someone else’s bed tonight” along with others accusing me of treating him poorly. The volume of texts I received from him was borderline harassment and a lot of them were incomprehensible, leading me to believe he was beyond intoxicated, and eventually resulted in me turning off my phone. The next morning he called at 8 a.m. and sincerely apologized. I explained how he had hurt me and I had seen a side of him I never knew existed, as well as that I had lost trust in him. I told him I needed some space and that I didn’t want to talk to him until we both return home at the end of the week, and we could figure out where to go from here in person. Since then, he has been texting apologies periodically, has said that I did nothing to deserve that treatment and that the threat to cheat was an empty threat. Is this a red flag, or a fluke, and how should I move forward from this? — Blind Sided

I wouldn’t say this is necessarily a red flag or a fluke, but instead a wonderful opportunity to further the lines of communication and build up trust between you. One of the ways we learn who is most trustworthy in our inner circles is watching how they react when they see the ugliest sides of us. We all have ugly sides and eventually, if you’re with someone long enough, those ugly parts are going to rear their nasty heads. So, you’ve now seen an ugly side to your boyfriend that you didn’t know existed and you have to determine whether it’s a side you’re willing to accept and love him in spite of or if the ugliness is too great for you to accept.

Only you can determine for yourself whether your boyfriend’s drunken behavior was enough to call it quits with him. You have to weigh the length of time you’ve been together, the emotions invested, and whether you have substantial enough reason to believe this rare behavior is not indicative of a larger issue (and if it is, is it an issue you’re willing to tackle?). If it were me — and it’s not, and I’m only going on the details you’ve provided — I’d be inclined to give your boyfriend another chance, but to remain on guard. I’d clearly express how out of line I thought he was and that if anything like that ever happened again, it would be over. But I’d keep the larger picture in mind — the year-and-a-half relationship that has otherwise been kind and loving up to now. I’d also remember that it’s natural to feel a little territorial over a significant other and that I wouldn’t really be pleased if my boyfriend were sharing a bed with another woman. And I’d keep in mind that if he was out drinking with college friends, he probably shared what happened and was egged on by the other guys. He probably bought into the mob mentality and acted out in reaction to that. Those aren’t excuses, but they may be explanations beyond a simple “He has issues.” Are they good enough explanations for you? Are you willing to overlook one night of bad behavior in light of a great year-and-a-half together? Those are questions only you can answer. But my opinion is this is not a clear MOA situation at all.

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